Hydrochloric Acid → 2-(4-(Methoxycarbonyl)-2-methylphenyl)acetic acid

HRID 410041Notes

Reaction equation

HRID 410041 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1[CH3:16])C.O.[Li+].[OH-].Cl>CO>[CH3:13][O:12][C:10]([C:9]1[CH:14]=[CH:15][C:6]([CH2:5][C:4]([OH:17])=[O:3])=[C:7]([CH3:16])[CH:8]=1)=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 67365879Methyl 4-(2-ethoxy-2-oxoethyl)-3-methylbenzoate

Product 1

HCID 575552242-(4-(Methoxycarbonyl)-2-methylphenyl)acetic acidYield 91.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-(2-ethoxy-2-oxoethyl)-3-methylbenzoate (366 mg) was suspended in MeOH (10 ml) and H2O (2 ml) and treated with LiOH (48 mg) over 3 days. After the reaction mixture was acidified with 1N HCl, the product was extracted with EtOAc. Evaporation and drying in vacuum afforded the desired product (295 mg).

Workup

  1. extractionthe product was extracted with EtOAc
  2. customEvaporation
  3. customdrying in vacuum

Sources & evidence

ORD record
ord-a479f492c6764007a2bacc19846ab445
Source dataset
uspto-grants-2014_06
Patent number
US08759548B2

Reaction notes

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