Methanol → (S)-Cyclopent-1-enyl-hydroxyphenylacetic acid

Participants

Role	Name	HCID	Charge
Reactant	Methanol	HCID 887	—
Reactant	Water	HCID 962	—
Reactant	Potassium Hydroxide	HCID 14797	—
Reactant	(2R,5S)-2-t-Butyl-5-cyclopent-1-enyl-5-phenyl-1,3-dioxolan-4-one	HCID 67242157	—
Solvent	Ammonium Chloride	HCID 25517	—
Product	(S)-Cyclopent-1-enyl-hydroxyphenylacetic acid	HCID 67241271	69.9%

Reaction Conditions

Temperature	130 °C

Reaction Steps

Intermediate (1c) (540 mg, 1.9 mmol) was dissolved in MeOH (927 μL, 22.9 mmol). Water (1.84 mL, 102 mmol) was added, followed by the addition of KOH (1.1 g, 18.8 mmol). The reaction was refluxed at 130° C. for 3 hours. The mixture was diluted to 250 mL with saturated ammonium chloride, then washed (2×100 mL hexane). The remaining aqueous emulsion was washed (2×250 mL EtOAc). The EtOAc layers were combined, washed with 50 mL saturated aqueous NaCl, dried over Na2SO4, filtered and concentrated to yield intermediate (1d) as a brownish-yellow solid (290 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08198304B2
Source dataset	uspto-grants-2012_06
ORD ID	ord-4eea701007fd4b9eaa232e02eecf031c
Source note	uspto-grants-2012_06