Ethanol → alpha-(Difluoromethyl)-4-methylbenzenemethanol

HRID 359209ノート

反応式

HRID 359209 の反応式
[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]

参加物

8

反応物 4

HCID 702EthanolHCID 887MethanolHCID 5360545Sodium2 回HCID 14291991HCID 14291991、化合物

生成物 1

HCID 10057975alpha-(Difluoromethyl)-4-methylbenzenemethanol収率 49%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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 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).

後処理

  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

出典と根拠

ORDレコード
ord-b36465d08bf847769772b94db8857c28
出典データセット
uspto-grants-1991_03
特許番号
US04999429

反応ノート

読み込み中…