Ethanol → alpha-(Difluoromethyl)-4-methylbenzenemethanol

HRID 1904520노트

반응식

HRID 1904520 반응식
[F:1][C:2]([F:21])(S(C1C=CC=CC=1)(=O)=O)[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)[OH:4].C(O)C.[Na].CO>O1CCCC1.Cl.O>[F:1][CH:2]([F:21])[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)[OH:4]

참가 물질

8

반응물 4

HCID 702EthanolHCID 887MethanolHCID 5360545Sodium2회HCID 14291991HCID 14291991, 화합물

생성물 1

HCID 10057975alpha-(Difluoromethyl)-4-methylbenzenemethanol수율 49%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2.0 g (6.4 mmol) of 2,2-difluoro-1-(4-methylphenyl)-2-phenylsulfonylethanol and 1.9 mL (32 mmol) of absolute ethanol in 20 mL of dry tetrahydrofuran was treated with 0.74 g (32 mmol) of sodium spheres. After 90 minutes 1 mL of methanol followed by 1 mL of water were added to decompose unreacted sodium, and the mixture was poured into 100 mL of IN HCl. The resulting aqueous mixture was extracted with three 50 mL portions of dichloromethane. Combination, drying (MgSO4), and concentration of the organic layers afforded an orange liquid which was short path distilled to give 0.54 g (49% yield) of 2,2-difluoro-1-(4-methylphenyl)ethanol; bp 58 C at 0.6 torr (lit 7 60-62.C at 0.5-0.6 torr; DePuy et al., J. Org. Chem., 1974, 39, 878); mass spectrum (70 eV) m/e (relative intensity) 172 (17, M+), 121 (100), 93 (68), 91 (75), 77 (64), 65 (25), 51 (46), 39 (24).

후처리

  1. additionwere added
  2. extractionThe resulting aqueous mixture was extracted with three 50 mL portions of dichloromethane
  3. dry with materialCombination, drying (MgSO4), and concentration of the organic layers
  4. customafforded an orange liquid which
  5. distillationdistilled

출처 및 근거

ORD 기록
ord-b33ed3a2c4f54b29b819007abeaa1d02
출처 데이터셋
uspto-grants-1989_06
특허 번호
US04837327

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