Water → Acetic Acid 3-(4-tert-butyl-phenyl)-2-methyl-propenyl Ester

HRID 1169170Notes

Reaction equation

HRID 1169170 reaction equation
[CH3:1][CH:2]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][CH:7]=1)[CH:3]=[O:4].C(N(CC)CC)C.[C:23]([O-])(=[O:25])[CH3:24].[Na+].O>C(OC(=O)C)(=O)C>[C:12]([C:9]1[CH:8]=[CH:7][C:6]([CH2:5][C:2]([CH3:1])=[CH:3][O:4][C:23](=[O:25])[CH3:24])=[CH:11][CH:10]=1)([CH3:14])([CH3:13])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 228987LilialHCID 517045Sodium Acetate

Product 1

HCID 53757095Acetic Acid 3-(4-tert-butyl-phenyl)-2-methyl-propenyl EsterYield 459.7%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 200 g 2-methyl-3-(4-tert-butylphenyl)-propanal, 280 ml triethylamine and 13.4 g sodium acetate in 800 ml of acetic anhydride was stirred at 120° C. for 5.5 hours. Then the solution was cooled, water was added and the water phase was extracted with hexane. The organic phase was washed with 2N NaOH and water to neutrality, dried and evaporated to dryness. The residue was distilled to yield 185 g of a colorless liquid.

Workup

  1. temperatureThen the solution was cooled
  2. extractionthe water phase was extracted with hexane
  3. washThe organic phase was washed with 2N NaOH and water to neutrality
  4. customdried
  5. customevaporated to dryness
  6. distillationThe residue was distilled

Sources & evidence

ORD record
ord-13aef4d1e1244bc099d5bd2216e81f66
Source dataset
uspto-grants-2003_09
Patent number
US06627763B2

Reaction notes

Loading…