Methanol → Methyl 4-acetylbenzoate

HRID 34740

Reaction equation

HRID 34740 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].OS(O)(=O)=O.[CH3:18]O>>[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:10][CH3:18])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 114704-Acetylbenzoic Acid

Product 1

HCID 137990Methyl 4-acetylbenzoate

Procedure

4-Acetylbenzoic acid (12.7 g., 0.077 mol) was dissolved in 750 ml. methanol. Concentrated H2SO4 (1.6 ml.) was added and the mixture heated at 70° for 8 hours, cooled, stripped solids, taken up in 400 ml. ether, washed 3×150 ml. saturated NaHCO3 and 1×150 ml. brine, dried over MgSO4 and stripped to yield title product, 12.9 g.; tlc Rf 0.46 (2:1 hexane:ethyl acetate).

Workup

  1. temperaturethe mixture heated at 70° for 8 hours
  2. temperaturecooled
  3. washether, washed 3×150 ml
  4. dry with materialbrine, dried over MgSO4

Sources & evidence

ORD record
ord-fc6ba0155df54434845b93f9b793b887
Source dataset
uspto-grants-1988_08
Patent number
US04762921

Linked notes

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