Hydrochloric Acid → (4-Carboxymethoxyphenyl)-4-methoxyphenylcarbinol

HRID 1649955Notes

Reaction equation

HRID 1649955 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([C:9]2[CH:19]=[CH:18][C:12]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.[BH4-].[Na+].Cl>CO.CN1CCOCC1>[C:15]([CH2:14][O:13][C:12]1[CH:11]=[CH:10][C:9]([CH:7]([C:6]2[CH:20]=[CH:21][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[OH:8])=[CH:19][CH:18]=1)([OH:17])=[O:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 143045424-(4-Methoxybenzoyl)phenoxyacetic acid

Product 1

HCID 13966820(4-Carboxymethoxyphenyl)-4-methoxyphenylcarbinol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 79724-MethylmorpholineSolvent

Procedure

11.2 g of 4-(4-methoxybenzoyl)phenoxyacetic acid are dissolved in 600 ml of 80% strength methanol (reflux), and 4.4 ml of N-methylmorpholine are added. 6 g of sodium borohydride are added in portions over the course of two hours, and the reaction is continued under reflux conditions for 3 hours. The mixture is cooled to room temperature and acidified to pH 2.5 with 3N HCl. The methanol is distilled off, the aqueous phase is extracted with ethyl acetate, and the organic phase is washed with brine and dried over sodium sulfate. After removal of the ethyl acetate by distillation there remains a white amorphous powder. The product is used directly for the next reaction.

Workup

  1. additionare added
  2. distillationThe methanol is distilled off
  3. extractionthe aqueous phase is extracted with ethyl acetate
  4. washthe organic phase is washed with brine
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of the ethyl acetate
  7. distillationby distillation
  8. customThe product is used directly for the next reaction

Sources & evidence

ORD record
ord-8bed4e1881904129ba0bbf6e1c56e831
Source dataset
uspto-grants-1990_05
Patent number
US04922015

Reaction notes

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