Hydrochloric Acid → Mosher's acid

HRID 1275927Notes

Reaction equation

HRID 1275927 reaction equation
[CH3:1][O:2][C:3]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:8]([F:11])([F:10])[F:9])[C:4]([O:6]C)=[O:5].[OH-].[Na+].Cl>CO>[CH3:1][O:2][C:3]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:8]([F:11])([F:10])[F:9])[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 604963Methyl 3,3,3-trifluoro-2-methoxy-2-phenylpropanoate

Product 1

HCID 86531Mosher's acidYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

210 g of methyl α-methoxy-α-trifluoromethylphenylacetate (obtained according to Example 1) were mixed with 600 ml of methanol at 25° C., and 860 ml of 1N aqueous sodium hydroxide solution were slowly added dropwise. The mixture was stirred at room temperature for 5 hours. Dilute aqueous hydrochloric acid was then used to adjust the pH to 1, and extraction was carried out using 2×200 ml of methylene chloride, the organic phase was dried over sodium sulphate and, finally, the solvent was removed. This gave 96% yield of α-methoxy-α-trifluoromethylphenylacetic acid (=190 g).

Workup

  1. extractionto 1, and extraction
  2. dry with materialthe organic phase was dried over sodium sulphate
  3. customfinally, the solvent was removed

Sources & evidence

ORD record
ord-27b0a1f500144cac86377d98667bf123
Source dataset
uspto-grants-2000_12
Patent number
US06162943

Reaction notes

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