Vinyl benzoate → Benzoic Acid

Temperatur

100 °C

A 70 mL stainless steel high pressure reactor fitted with a Pyrex glass liner and magnetic stir bar is charged with THF (5 mL), (PPh3)2PdCl2 (0.05 mmol), L-menthoxyethanol (0.5 mmol), and vinyl benzoate (0.5 mmol). The reactor is sealed, pressurized to 1000 psig with CO, and stirred for 24 hours at 100° C. The product mixture, isolated after removal of gas from the reactor vessel, contains a diastereomeric mixture of L-menthoxyethyl benzoyl-L-lactate and L-menthoxyethyl benzoyl-D-lactate. The diastereomers are separated by preparative gas chromatography using an SE-30 liquid phase column. Each diastereomer is hydrolyzed separately by treatment with 2N HCl (aq) for 2 hours at 100° C. to give pure L- and D-lactic acid, benzoic acid, and L-menthoxyethanol, which is thereafter recycled to a repeat of the foregoing hydrocarboxylation reaction.

1. customA 70 mL stainless steel high pressure reactor fitted with a Pyrex glass liner and magnetic stir bar
2. customThe reactor is sealed
3. customThe product mixture, isolated
4. customafter removal of gas from the reactor vessel
5. additiona diastereomeric mixture of L-menthoxyethyl benzoyl-L-lactate and L-menthoxyethyl benzoyl-D-lactate
6. customThe diastereomers are separated by preparative gas chromatography
7. waitEach diastereomer is hydrolyzed separately by treatment with 2N HCl (aq) for 2 hours at 100° C.

ORD-Eintrag

ord-cef81fc65e9647529085aab47396ffb5

Quelldatensatz

uspto-grants-1988_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04749811