Benzyl Alcohol → HCID 131712948, compound

HRID 1757938Notes

Reaction equation

HRID 1757938 reaction equation
[C:1]1([C:7]2[CH2:11][CH:10]([C:12]([OH:14])=[O:13])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:17])=O.[CH2:19](O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[ClH:17].[C:1]1([C:7]2[CH2:11][CH:10]([C:12]([O:14][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:13])[NH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 244Benzyl Alcohol2×HCID 24386Thionyl Chloride2×HCID 131023953-Phenyl-4,5-dihydro-1H-pyrazole-5-carboxylic acid

Product 1

HCID 131712948HCID 131712948, compound

Procedure

20 g. of (+)-4,5-Dihydro-3-phenyl-1H-pyrazole-5-carboxylic acid is added at room temperature to a solution of 25 g. of thionyl chloride in 150 ml. of benzyl alcohol (prepared by adding the thionyl chloride to the benzyl alcohol at -5°) and allowed to stir for 48 hours. Hydrochloric acid is removed in vacuo and the remaining solution is poured into 250 ml. of anhydrous ether. The separated product is collected, washed with fresh ether, and dried to give (+)-4,5-dihydro-3-phenyl-1H-pyrazole-5-carboxylic acid, phenylmethyl ester, hydrochloride (1:1).

Workup

  1. customHydrochloric acid is removed in vacuo
  2. additionthe remaining solution is poured into 250 ml
  3. customThe separated product is collected
  4. washwashed with fresh ether
  5. customdried

Sources & evidence

ORD record
ord-adb25937e10644de89fd6f8aefac0f6d
Source dataset
uspto-grants-1983_02
Patent number
US04371526

Reaction notes

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