Methanol → Methyl 4-methylbenzoate

HRID 1579700Notes

Reaction equation

HRID 1579700 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH3:11][OH:12]>C1C=CC=CC=1>[CH3:11][O:12][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 134054-Methylbenzoyl Chloride

Product 1

HCID 7455Methyl 4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

544 g. of 4-methyl-benzoic acid was boiled with 550 ml. of thionyl chloride until a clear solution was obtained. After the excess thionyl chloride was distilled off, the residue was fractionated, yielding 605 g. of 4-methyl-benzoyl chloride; b.p. 91°/9 mm Hg., nD24 = 1.5532. This was dissolved in 550 ml. of absolute benzene and the so-formed solution added to a mixture of 248 ml. of absolute methanol and 550 ml. of absolute benzene. After the exothermic reaction had terminated, the reaction mixture was boiled for a further 20 hours, then concentrated in vacuo and the product, 4-methyl-benzoic acid methyl ester, isolated by conventional means. It could be purified by distillation, and the purified product boiled at 91°/9 mm Hg., m.p. 32°.

Workup

  1. distillationAfter the excess thionyl chloride was distilled off
  2. customyielding 605 g
  3. dissolutionThis was dissolved in 550 ml
  4. customAfter the exothermic reaction
  5. customhad terminated
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b483c89ed92c475397f27879a3f8ab0c
Source dataset
uspto-grants-1976_01
Patent number
US03931268

Reaction notes

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