Acetic Acid → 3-(Acetyloxy)-2-[(acetyloxy)methyl]-2-methylpropanoic acid

HRID 34518Notes

Reaction equation

HRID 34518 reaction equation
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH3:7])[C:4]([OH:6])=[O:5].[C:10](OC(=O)C)(=[O:12])[CH3:11].[C:17](O)(=[O:19])[CH3:18]>>[C:10]([O:1][CH2:2][C:3]([CH2:8][O:9][C:17](=[O:19])[CH3:18])([CH3:7])[C:4]([OH:6])=[O:5])(=[O:12])[CH3:11]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 78501Dimethylolpropionic acid

Product 1

HCID 224578423-(Acetyloxy)-2-[(acetyloxy)methyl]-2-methylpropanoic acid

Procedure

268 g (2 moles) of 2,2-bis-hydroxymethyl propionic acid are refluxed for 10 hours in 800 ml of glacial acetic acid and 416 ml (4.4 moles) of acetic acid anhydride. The reaction solution is freed from the solvent in vacuo. The oily residue is stirred with 1500 ml of petroleum ether, the carboxylic acid ester is crystallizing out. It is filtered off under suction and washed with petroleum ether. Yield 420 g (96% of the theoretical); Mp. 85° C.

Workup

  1. customthe carboxylic acid ester is crystallizing out
  2. filtrationIt is filtered off under suction
  3. washwashed with petroleum ether

Sources & evidence

ORD record
ord-514729e647c04c69a19605290443db05
Source dataset
uspto-grants-1988_08
Patent number
US04762777

Reaction notes

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