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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 896940Generated: October 25, 2026

Tetramethylammonium hydroxide → Lipoic acid

https://huagongshe.com/reaction/896940

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetramethylammonium hydroxideHCID 60966—
Reactant(R)-Dihydrolipoic acidHCID 9834298—
ReactantPotassium tert-butoxideHCID 23665647—
SolventDimethylformamideHCID 6228—
ProductLipoic acidHCID 6112—
Product(R)-Dihydrolipoic acidHCID 9834298—

Reaction Steps

In other synthetic schemes the base, tetramethylammonium hydroxide can be substituted for potassium t-butoxide in DMF. The former base though can be stored under air, whilst the latter needs to be kept in an inert atmosphere. The dihydrolipoic acid works best if it totally clear. If the reduction lipoic acid to produce dihydrolipoic acid is not complete, a yellow coloration of the solution will be evident. The yellow solution can be distilled (distills at 140° C. under vacuum) to yield a clear solution of dihydrolipoic acid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06921496B2
Source datasetuspto-grants-2005_07
ORD IDord-dfa8a8fbcaf8412da0e392ebd82dc423
Source noteuspto-grants-2005_07