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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2065437Generated: November 2, 2026

Acetic Acid → Benzoic acid, 4-hydroxy-, carboxymethyl ester

https://huagongshe.com/reaction/2065437

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantLithium HydroxideHCID 3939—
Reactant4-Hydroxy-benzoic acid tert-butoxycarbonylmethyl esterHCID 58427509—
SolventTetrahydrofuranHCID 8028—
ProductBenzoic acid, 4-hydroxy-, carboxymethyl esterHCID 58427513—

Reaction Conditions

Temperature55 °C

Reaction Steps

To a solution of 4-hydroxy-benzoic acid tert-butoxycarbonylmethyl ester 15 (18 grams, 71.42 mmol) in tetrahydrofuran (100 mL) is added 10% lithium hydroxide solution (35 mL). The mixture is heated at 50-60° C. for 1 hour. The reaction mass is cooled to room temperature, and the pH is adjusted to 4 with dilute acetic acid. The organic phase is separated and distilled to give crude 16, which can be purified in appropriate solvent.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08288505B2
Source datasetuspto-grants-2012_10
ORD IDord-16d564569f1d4bb6b4b547a8601f331f
Source noteuspto-grants-2012_10