3-butylbenzene-1,2-diol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 5.64 g (29 mM) of 4-n-butylveratrole, 18.54 g (309 mM) of acetic acid and 55.62 g (323 mM) of 47% hydrobromic acid was heated under reflux for 4 hours with stirring. The reaction mixture was cooled to the room temperature and added with 50 ml of eater. The separated oil was extracted with ether. The ether solution was successively washed with 50 ml of water, 75 g of 5% aqueous sodium thiosulfate solution, and further twice with each 50 ml of water. The resulting solution was dried with anhydrous sodium sulfate, distilled off ether, and vacuum distilled to obtain 3.89 g (23 mM) of n-butylcatechol as light yellow liquid having a boiling point of 125° C./3 mmHg. was heated under reflux for 4 hours added with 50 ml of eater The separated oil was extracted with ether The ether solution was successively washed with 50 ml of water, 75 g of 5% aqueous sodium thiosulfate solution The resulting solution was dried with anhydrous sodium sulfate distilled off ether, and vacuum distilled

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 5.64 g (29 mM) of 4-n-butylveratrole, 18.54 g (309 mM) of acetic acid and 55.62 g (323 mM) of 47% hydrobromic acid was heated under reflux for 4 hours with stirring. The reaction mixture was cooled to the room temperature and added with 50 ml of eater. The separated oil was extracted with ether. The ether solution was successively washed with 50 ml of water, 75 g of 5% aqueous sodium thiosulfate solution, and further twice with each 50 ml of water. The resulting solution was dried with anhydrous sodium sulfate, distilled off ether, and vacuum distilled to obtain 3.89 g (23 mM) of n-butylcatechol as light yellow liquid having a boiling point of 125° C./3 mmHg. was heated under reflux for 4 hours added with 50 ml of eater The separated oil was extracted with ether The ether solution was successively washed with 50 ml of water, 75 g of 5% aqueous sodium thiosulfate solution The resulting solution was dried with anhydrous sodium sulfate distilled off ether, and vacuum distilled

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 5.64 g (29 mM) of 4-n-butylveratrole, 18.54 g (309 mM) of acetic acid and 55.62 g (323 mM) of 47% hydrobromic acid was heated under reflux for 4 hours with stirring. The reaction mixture was cooled to the room temperature and added with 50 ml of eater. The separated oil was extracted with ether. The ether solution was successively washed with 50 ml of water, 75 g of 5% aqueous sodium thiosulfate solution, and further twice with each 50 ml of water. The resulting solution was dried with anhydrous sodium sulfate, distilled off ether, and vacuum distilled to obtain 3.89 g (23 mM) of n-butylcatechol as light yellow liquid having a boiling point of 125° C./3 mmHg. was heated under reflux for 4 hours added with 50 ml of eater The separated oil was extracted with ether The ether solution was successively washed with 50 ml of water, 75 g of 5% aqueous sodium thiosulfate solution The resulting solution was dried with anhydrous sodium sulfate distilled off ether, and vacuum distilled

反応条件: temp:240.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-(4-aminophenyl)ethanol (10 g, 73 mmol), KOH (25 g, 450 mmol) and t butylcatechol (0.1 g) was heated at 240° C./40 mmHg in a flask fitted with a water-cooled condenser for 90 minutes. The contents of the flask were then distilled into a receiver vessel as a clear, 2-phase system which sodified as white crystals on standing. The solid was extracted with 50 ml diethyl ether, washed twice with 25 ml distilled water and the organic phase separated. After drying for 2 hours over NaOH pellets, the ether solution was filtered and the volatiles removed in vacuo to yield a colourless crystalline solid. Fractional distillation at 38° C. (1×10-2 mbar) yielded 4-aminostyrene. The colourless liquid was stored at -30° C. (at which temperature it is a crystalline solid) to prevent polymerisation. cooled condenser for 90 minutes The contents of the flask were then distilled into a receiver vessel as a clear, 2-phase system which The solid was extracted with 50 ml diethyl ether washed twice with 25 ml distilled water the organic phase separated After drying for 2 hours over NaOH pellets the ether solution was filtered the volatiles removed in vacuo to yield a colourless crystalline solid Fractional distillation at 38° C. (1×10-2 mbar)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 5.64 g (29 mM) of 4-n-butylveratrole, 18.54 g (309 mM) of acetic acid and 55.62 g (323 mM) of 47% hydrobromic acid was heated under reflux for 4 hours with stirring. The reaction mixture was cooled to the room temperature and added with 50 ml of eater. The separated oil was extracted with ether. The ether solution was successively washed with 50 ml of water, 75 g of 5% aqueous sodium thiosulfate solution, and further twice with each 50 ml of water. The resulting solution was dried with anhydrous sodium sulfate, distilled off ether, and vacuum distilled to obtain 3.89 g (23 mM) of n-butylcatechol as light yellow liquid having a boiling point of 125° C./3 mmHg. was heated under reflux for 4 hours added with 50 ml of eater The separated oil was extracted with ether The ether solution was successively washed with 50 ml of water, 75 g of 5% aqueous sodium thiosulfate solution The resulting solution was dried with anhydrous sodium sulfate distilled off ether, and vacuum distilled

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 110 mg of butylpyrocatechol (as a polymerization inhibitor) and 180 g of dry Na2CO3 (anhydrous) are added to 167.4 g (0.8 mol) of dimethyl aminoterephthalate in 3 1 of acetone. 89 g (0.85 mol) of vinylacetyl chloride are added dropwise to this mixture at 35°-40 ° C. in the course of 20 minutes and the mixture is then boiled under reflux for 4 hours. The filtered solution is concentrated to 1 1 and the concentrate is crystallized in the cold. The crystals of dimethyl N-butenoylaminoterephthalate isolated are recrystallized once from 1.2 1 of methanol and then from a mixture of 426 ml of ethyl acetate and 344 ml of methanol. under reflux for 4 hours The filtered solution is concentrated to 1 1 the concentrate is crystallized in the cold

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 110 mg of butylpyrocatechol (as a polymerization inhibitor) and 180 g of dry Na2CO3 (anhydrous) are added to 167.4 g (0.8 mol) of dimethyl aminoterephthalate in 3 1 of acetone. 89 g (0.85 mol) of vinylacetyl chloride are added dropwise to this mixture at 35°-40 ° C. in the course of 20 minutes and the mixture is then boiled under reflux for 4 hours. The filtered solution is concentrated to 1 1 and the concentrate is crystallized in the cold. The crystals of dimethyl N-butenoylaminoterephthalate isolated are recrystallized once from 1.2 1 of methanol and then from a mixture of 426 ml of ethyl acetate and 344 ml of methanol. under reflux for 4 hours The filtered solution is concentrated to 1 1 the concentrate is crystallized in the cold

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 110 mg of butylpyrocatechol (as a polymerization inhibitor) and 180 g of dry Na2CO3 (anhydrous) are added to 167.4 g (0.8 mol) of dimethyl aminoterephthalate in 3 1 of acetone. 89 g (0.85 mol) of vinylacetyl chloride are added dropwise to this mixture at 35°-40 ° C. in the course of 20 minutes and the mixture is then boiled under reflux for 4 hours. The filtered solution is concentrated to 1 1 and the concentrate is crystallized in the cold. The crystals of dimethyl N-butenoylaminoterephthalate isolated are recrystallized once from 1.2 1 of methanol and then from a mixture of 426 ml of ethyl acetate and 344 ml of methanol. under reflux for 4 hours The filtered solution is concentrated to 1 1 the concentrate is crystallized in the cold

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 5.64 g (29 mM) of 4-n-butylveratrole, 18.54 g (309 mM) of acetic acid and 55.62 g (323 mM) of 47% hydrobromic acid was heated under reflux for 4 hours with stirring. The reaction mixture was cooled to the room temperature and added with 50 ml of eater. The separated oil was extracted with ether. The ether solution was successively washed with 50 ml of water, 75 g of 5% aqueous sodium thiosulfate solution, and further twice with each 50 ml of water. The resulting solution was dried with anhydrous sodium sulfate, distilled off ether, and vacuum distilled to obtain 3.89 g (23 mM) of n-butylcatechol as light yellow liquid having a boiling point of 125° C./3 mmHg. was heated under reflux for 4 hours added with 50 ml of eater The separated oil was extracted with ether The ether solution was successively washed with 50 ml of water, 75 g of 5% aqueous sodium thiosulfate solution The resulting solution was dried with anhydrous sodium sulfate distilled off ether, and vacuum distilled

反応条件: temp:240.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-(4-aminophenyl)ethanol (10 g, 73 mmol), KOH (25 g, 450 mmol) and t butylcatechol (0.1 g) was heated at 240° C./40 mmHg in a flask fitted with a water-cooled condenser for 90 minutes. The contents of the flask were then distilled into a receiver vessel as a clear, 2-phase system which sodified as white crystals on standing. The solid was extracted with 50 ml diethyl ether, washed twice with 25 ml distilled water and the organic phase separated. After drying for 2 hours over NaOH pellets, the ether solution was filtered and the volatiles removed in vacuo to yield a colourless crystalline solid. Fractional distillation at 38° C. (1×10-2 mbar) yielded 4-aminostyrene. The colourless liquid was stored at -30° C. (at which temperature it is a crystalline solid) to prevent polymerisation. cooled condenser for 90 minutes The contents of the flask were then distilled into a receiver vessel as a clear, 2-phase system which The solid was extracted with 50 ml diethyl ether washed twice with 25 ml distilled water the organic phase separated After drying for 2 hours over NaOH pellets the ether solution was filtered the volatiles removed in vacuo to yield a colourless crystalline solid Fractional distillation at 38° C. (1×10-2 mbar)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 5.64 g (29 mM) of 4-n-butylveratrole, 18.54 g (309 mM) of acetic acid and 55.62 g (323 mM) of 47% hydrobromic acid was heated under reflux for 4 hours with stirring. The reaction mixture was cooled to the room temperature and added with 50 ml of eater. The separated oil was extracted with ether. The ether solution was successively washed with 50 ml of water, 75 g of 5% aqueous sodium thiosulfate solution, and further twice with each 50 ml of water. The resulting solution was dried with anhydrous sodium sulfate, distilled off ether, and vacuum distilled to obtain 3.89 g (23 mM) of n-butylcatechol as light yellow liquid having a boiling point of 125° C./3 mmHg. was heated under reflux for 4 hours added with 50 ml of eater The separated oil was extracted with ether The ether solution was successively washed with 50 ml of water, 75 g of 5% aqueous sodium thiosulfate solution The resulting solution was dried with anhydrous sodium sulfate distilled off ether, and vacuum distilled