Methanol → Methyl 4-phenylbutyrate

HRID 602039Notes

Reaction equation

HRID 602039 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[CH3:18]O>O>[CH3:18][O:11][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 47754-Phenylbutyric Acid

Product 1

HCID 281254Methyl 4-phenylbutyrateYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
49 °C

Procedure

1800 g (10.98 moles) of 4-phenylbutyric acid, crystalline in a glass bottle was heated with a heating blanket for 2 h to melt the acid. The liquid was poured in 8 L of methanol in a 22 L reaction flask (3-necked round-bottom flask fitted with stirrer and thermometer adapters). The solution was stirred under Argon, temperature 20° C.-33° C., and 400 mL concentrated sulfuric acid was added in 50 mL portions. The temperature increased to 49° C. The solution was stirred under argon over the week-end and allowed to cool to ambient temperature. The solution was transferred to a quench tank and diluted with 8 L of water. The oil formed was separated and the aqueous phase was extracted with 2×1 L of ethyl acetate. The extracts were combined with the oil and the solution concentrated to give 1753 g of clear oil in 90% yield.

Workup

  1. stirringThe solution was stirred under argon over the week-end
  2. temperatureto cool to ambient temperature
  3. customThe oil formed
  4. customwas separated
  5. extractionthe aqueous phase was extracted with 2×1 L of ethyl acetate
  6. concentrationthe solution concentrated

Sources & evidence

ORD record
ord-d6e2ff1607b449449a04f3881b867c8a
Source dataset
uspto-grants-2011_03
Patent number
US07902394B2

Reaction notes

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