Acetic Acid → 2-(3,4-Dichlorophenyl)-3-(1,3-dioxolan-2-yl)propan-1-ol

HRID 1533035노트

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HRID 1533035 반응식
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]([CH2:14][CH:15]2[O:19][CH2:18][CH2:17][O:16]2)[CH:12]=[O:13])[CH:7]=[CH:8][C:9]=1[Cl:10].C(O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O.ClCCl>[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]([CH2:14][CH:15]2[O:16][CH2:17][CH2:18][O:19]2)[CH2:12][OH:13])[CH:7]=[CH:8][C:9]=1[Cl:10]

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 4311764Sodium borohydrideHCID 226137992-(3,4-Dichlorophenyl)-3-(1,3-dioxolan-2-yl)propan-1-al

생성물 1

HCID 226137962-(3,4-Dichlorophenyl)-3-(1,3-dioxolan-2-yl)propan-1-ol수율 101.3%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

Sodium borohydride (5 g) was added in two portions, over 40 minutes, to an ice-cooled solution of 2-(3,4-dichlorophenyl)-3-(1,3-dioxolan-2-yl)propan-1-al (53.5 g) (see Preparation 14) in ethanol (300 ml). The mixture was stirred for a further 30 minutes before removing the solvent under reduced pressure to give a residue. This was suspended in water (200 ml), cooled to 0° C. and the mixture acidified (pH<6) with glacial acetic acid. Dichloromethane was added and the aqueous phase basified (pH>8) by addition of solid sodium carbonate. A further amount of dichloromethane (200 ml) was added and the organic and aqueous phases separated. The aqueous phase was further extracted with dichloromethane (200 ml). The organic phases were combined, washed with brine, dried over anhydrous sodium sulphate and the solvent removed under reduced pressure to give 2-(3,4-dichlorophenyl)-3-(1,3-dioxolan-2-yl)propan-1-ol (54.6 g) as a yellow oil.

후처리

  1. custombefore removing the solvent under reduced pressure
  2. customto give a residue
  3. customthe organic and aqueous phases separated
  4. extractionThe aqueous phase was further extracted with dichloromethane (200 ml)
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. customthe solvent removed under reduced pressure

출처 및 근거

ORD 기록
ord-c5824070b2af41418c50b93b9a37018f
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06207678B1

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