Hydrochloric Acid → alpha-(Difluoromethyl)-4-methylbenzenemethanol

HRID 1682342ノート

反応式

HRID 1682342 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].Cl>O1CCCC1.O.CO>[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 313Hydrochloric AcidHCID 702EthanolHCID 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 887Methanol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 L 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 1N HCl. The resulting aqueous mixture was extracted with three 50 m 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. Oro. 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 m 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-eb074cfb2929499a919a7a0e360522a1
出典データセット
uspto-grants-1992_12
特許番号
US05175302

反応ノート

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