Water → 4-Vinylcyclohexyl formic acid methyl ester

To a mixture of 25.2 g (70.5 mmol) of methyltriphenylphosphonium bromide with 125 ml of tetrahydrofuran (THF) was added 7.9 g (70.5 mmol) of potassium-tert-butoxide (t-BuOK) while being kept at a temperature lower than −20° C. and stirred at the same temperature for 1 hour. Then, 50 ml of solution of 10.0 g (58.8 mmol) of methyl 4-formylcyclohexanecarboxylate in THF was added dropwise to the reaction solution while being kept at a temperature lower than −20° C. and stirred at the same temperature for 2 hours. After finishing of the reaction, 50 ml of water was added to the reaction mixture and then the product was extracted with 200 ml of toluene. The organic layer thus obtained was washed with water thrice and then dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure and the residue thus obtained was subjected to silica gel column chromatography (eluent: toluene) to obtain 6.8 g of a crude methyl 4-vinylcyclohexanecarboxylate.

1. customwhile being kept at a temperature lower than −20° C.
2. customwhile being kept at a temperature lower than −20° C.
3. stirringstirred at the same temperature for 2 hours
4. additionwas added to the reaction mixture
5. extractionthe product was extracted with 200 ml of toluene
6. customThe organic layer thus obtained
7. washwas washed with water thrice
8. dry with materialdried over anhydrous magnesium sulfate
9. distillationThe solvent was distilled off under a reduced pressure
10. customthe residue thus obtained

ORD record

ord-0aa6db83489c4b0381a7f8b60edf124f

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06231934B1