Diethyl Ether → alpha-(4-Fluorophenyl)-1,2-benzenedimethanol

HRID 345565

반응식

HRID 345565 반응식
O(CC)CC.[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:12][C:13]1[CH:29]=[CH:28][C:16]([C:17]([C:19]2[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=2[C:21](O)=[O:22])=[O:18])=[CH:15][CH:14]=1.[OH-].[Na+]>O>[F:12][C:13]1[CH:29]=[CH:28][C:16]([CH:17]([C:19]2[C:20]([CH2:21][OH:22])=[CH:24][CH:25]=[CH:26][CH:27]=2)[OH:18])=[CH:15][CH:14]=1

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 820992-(4-Fluorobenzoyl)benzoic acidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 14230258alpha-(4-Fluorophenyl)-1,2-benzenedimethanol

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

To 1190 parts of 1,1'-oxybisethane were added at once 50 parts of lithium aluminium hydride. Then there was added dropwise a solution of 213.7 parts of 2-(4-fluorobenzoyl)benzoic acid in 875 parts of 1,1'-oxybixethane so that the mixture was kept at reflux temperature. Upon completion, stirring was continued first for 30 minutes at room temperature, then for 2 hours at reflux and further overnight at room temperature. The reaction mixture was cooled to 0° C. and there were added dropwise successively 50 parts of water, 50 parts of a 15% sodium hydroxide solution and 150 parts of water all at 0° C. The reaction mixture was filtered over Hyflo and washed thoroughly with 1,1'-oxybisethane. The organic phase was separated, washed with water, dried, filtered and evaporated. The residue was crystallized from a mixture of benzene and hexane, yielding 170.4 parts of α-(4-fluorophenyl)-1,2-benzenedimethanol; mp. ±75° C. (intermediate 91).

후처리

  1. temperatureat reflux temperature
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. filtrationThe reaction mixture was filtered over Hyflo
  4. washwashed thoroughly with 1,1'-oxybisethane
  5. customThe organic phase was separated
  6. washwashed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was crystallized from a mixture of benzene and hexane

출처 및 근거

ORD 기록
ord-83002c2fecf54737a80502cb8ef1e28a
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05057525

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