반응 #700932
ord-681f1ea58dc9427f8dfadf5d9d5628db
반응 방정식
반응 조건
후처리
- 1workup.STIRRINGstirring
- 2workup.WAITcontinued for 18 hours
- 3온도was cooled in ice
- 4기타The organic layer was separated
- 5추출the aqueous extracted with ethyl acetate
- 6세척The combined organic extracts were washed with brine
- 7건조dried (MgSO4)
- 8기타The solvent was removed in vacuo
- 9기타to give a pale yellow oil
- 10온도the mixture was heated
- 11온도at reflux for 1 hour
- 12기타The volatiles were removed in vacuo
- 13세척washed with ethyl acetate
- 14추출extracted with ethyl acetate
- 15세척this ethyl acetate was washed with water
- 16건조dried (MgSO4)
- 17기타the volatiles removed in vacuo
실험 절차
2-(4Chlorophenyl)ethanol (10 g) was stirred in 50% aqueous sodium hydroxide (70 ml), tetrabutylammoniumbromide (1.4 g) was added and the mixture stirred for 1 hour. t-Butylbromoacetate (28.6 ml) in toluene (140 ml) was added and stirring continued for 18 hours. Water (50 ml) was added and after 2 hours the mixture was cooled in ice and acidified to pH 1 with concentrated hydrochloric acid. The organic layer was separated and the aqueous extracted with ethyl acetate. The combined organic extracts were washed with brine and dried (MgSO4). The solvent was removed in vacuo to give a pale yellow oil This was dissolved in dichoromethane (100 ml) and trifluoroacetic acid (100 ml) added, the mixture was heated at reflux for 1 hour. The volatiles were removed in vacuo and the residue taken up in sodium hydroxide and washed with ethyl acetate. The aqueous layer was then acidified with concentrated hydrochloric acid and extracted with ethyl acetate, this ethyl acetate was washed with water, dried (MgSO4) and the volatiles removed in vacuo to provide the subtitle compound as a buff solid (16.4 g) which was used without further purification.