Glycolic Acid → (Propionyloxy)acetic acid

Reaction equation

[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[OH:6][CH2:7][C:8]([OH:10])=[O:9]>>[C:1]([O:6][CH2:7][C:8]([OH:10])=[O:9])(=[O:4])[CH2:2][CH3:3]

Participants

Reactant 2

HCID 757Glycolic Acid2×

HCID 62324Propionyl chloride

Product 1

HCID 12136775(Propionyloxy)acetic acid

Procedure

a solution consisting of propionyl chloride (64.7 g, 0.7 mol) and hydroxyacetic acid (19.0 g, 0.25 mol) is heated at 40° C., until the hydroxyacetic acid has completely dissolved. The excess propionyl chloride is then distilled off and 35.6 g of crude product containing 82% of (propionyloxy)acetic acid is obtained as a colorless liquid. The crude product can be used in the subsequent reaction without further purification.

Workup

dissolutionhas completely dissolved
distillationThe excess propionyl chloride is then distilled off
addition35.6 g of crude product containing 82% of (propionyloxy)acetic acid
customis obtained as a colorless liquid

Sources & evidence

ORD record: ord-507d3a629a8e4d0f8d464525d6f98f48
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07064102B2

Reaction notes

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