Hydrochloric Acid → Methyl 2,4,5-trimethylphenylacetate

HRID 1635904Notes

Reaction equation

HRID 1635904 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[CH:4][C:3]=1[CH2:10][C:11]([OH:13])=[O:12].Cl.[CH3:15]O>>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[CH:4][C:3]=1[CH2:10][C:11]([O:13][CH3:15])=[O:12]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2989242-(2,4,5-Trimethylphenyl)acetic acid

Product 1

HCID 22336857Methyl 2,4,5-trimethylphenylacetate

Procedure

100 g (0.56 mol) of 2,4,5-trimethylphenylacetic acid were dissolved in 230 ml of methanol, 6 ml of concentrated hydrochloric acid were added and the mixture was heated under reflux for 10 hours. It was then cooled to room temperature and the methanol was removed in vacuo. The residue was stirred into a solution of 53 g of sodium carbonate, dissolved in 260 ml of water, and the organic phase was taken up in 200 ml of toluene. The organic phase was separated off, dried and concentrated and the residue was distilled. 48.6 g of methyl 2,4,5-trimethylphenylacetate having a boiling point of 86° C. under 0.2 mbar were obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 10 hours
  3. customthe methanol was removed in vacuo
  4. dissolutiondissolved in 260 ml of water
  5. customThe organic phase was separated off
  6. customdried
  7. concentrationconcentrated
  8. distillationthe residue was distilled

Sources & evidence

ORD record
ord-225f6a712526409195885c165ac4f6b0
Source dataset
uspto-grants-2003_01
Patent number
US06511942B1

Reaction notes

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