Oxolane--water (1/1) → 4-(1-Methoxycarbonyl-1-methyl-ethyl)-benzoic acid

HRID 971167Notes

Reaction equation

HRID 971167 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13](Cl)=[O:14])=[CH:9][CH:8]=1)([CH3:6])[CH3:5].C1C[O:20]CC1.O>>[CH3:1][O:2][C:3]([C:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([OH:20])=[O:14])=[CH:9][CH:8]=1)([CH3:6])[CH3:5])=[O:16]

Participants

3

Reactant 2

HCID 21881883Oxolane--water (1/1)HCID 251112122-(4-Chlorocarbonylphenyl)-2-methylpropionic acid methyl ester

Product 1

HCID 251112114-(1-Methoxycarbonyl-1-methyl-ethyl)-benzoic acid

Conditions

Temperature
60 °C

Procedure

The product obtained from Example 193, Step C (240.0 mg, 1.0 mmol) was treated with THF/H2O (1:1, 10 ml). The mixture was stirred at 60° C. for 2 hr. The reaction mixture was extracted with EtOAc, washed with 1N HCl, H2O and brine. Reverse phase HPLC purification provided 4-(1-methoxycarbonyl-1-methyl-ethyl)-benzoic acid as white solid. MS found: (M+1)+=223.1.

Workup

  1. extractionThe reaction mixture was extracted with EtOAc
  2. washwashed with 1N HCl, H2O and brine
  3. customReverse phase HPLC purification

Sources & evidence

ORD record
ord-3cd973ed574d43e7a9511f001f3f7d7d
Source dataset
uspto-grants-2007_12
Patent number
US07312214B2

Reaction notes

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