Hydrochloric Acid → (R)-4-methylcyclohex-3-enecarboxylic acid

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Lithium hydroxide, monohydrate	HCID 168937	—
Reactant	(R)-((S)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl) 4-methylcyclohex-3-enecarboxylate	HCID 67984054	—
Solvent	Methanol	HCID 887	—
Solvent	Water	HCID 962	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	(R)-4-methylcyclohex-3-enecarboxylic acid	HCID 11040781	102.2%

Reaction Conditions

Temperature	50 °C

Reaction Steps

(R)—((S)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl) 4-methylcyclohex-3-enecarboxylate 502 (1.30 g, 5.15 mmol) in THF (10 mL), water (1 mL) and methanol (1 mL) was treated with lithium hydroxide monohydrate (2.16 g, 51.5 mmol) and warmed to 50° C. with stirring. After 1 hour, the reaction mixture treated with 1M HCl. The mixture was extracted with hexanes:THF (10:1), dried over sodium sulfate, filtered and concentrated to 0.738 g (quantitative yield) of (R)-4-methylcyclohex-3-enecarboxylic acid 503 as a white powder.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09393256B2
Source dataset	uspto-grants-2016_07
ORD ID	ord-aec370a1b79246398725be01d5f6b84a
Source note	uspto-grants-2016_07