Methanol → Methyl p-tert-butylbenzoate

HRID 1156093

Reaction equation

HRID 1156093 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:14]O.S(=O)(=O)(O)O>ClC(Cl)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([O:11][CH3:14])=[O:10])=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 74034-tert-Butylbenzoic acid

Product 1

HCID 97433Methyl p-tert-butylbenzoate

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

The reactant ester, methyl p-(t-butyl)-benzoate is prepared by refluxing a mixture of 178 g (1 mol) p-t-butyl benzoic acid, 96 g (3 mol) methanol, 300 ml dichloroethane, and 15 ml concentrated sulfuric acid for a 21 hour period. This mixture is washed four times with 500 ml water and 500 ml of a 10% sodium carbonate solution. The product is dried over calcium chloride and distilled, yielding 161 g of the ester boiling at 258°-262° C.

Workup

  1. temperatureby refluxing
  2. washThis mixture is washed four times with 500 ml water and 500 ml of a 10% sodium carbonate solution
  3. dry with materialThe product is dried over calcium chloride
  4. distillationdistilled

Sources & evidence

ORD record
ord-79f2944106f54e08accdf990781be915
Source dataset
uspto-grants-1982_06
Patent number
US04334015

Linked notes

Loading…