Tetrahydrofuran → Methyl 4-formylcyclohexane-1-carboxylate

To dried MTP 50.0 g (146 mmol), THF 500 ml was added, and potassium-t-butoxide 18.0 g (160 mmol) was added. The mixture was stirred for about one hour. To the reactant, a THF solution (100 ml) of 4-oxocyclohexane carboxylic acid methylester 21.9 g (140 mmol) was added dropwise, and the mixture was stirred for 2 hours. Water 500 ml was added to the reactant, the product was extracted with diethylether. The extract was washed with a sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (eluent: toluene). Such resulting purified material was stirred in mixed solvent of 2N-hydrochloric acid 500 ml and acetone 500 ml for 5 hours at room temperature, and the product was extracted with toluene. The extract was washed with a saturated sodium bicarbonate aqueous solution and then with water, and dried over anhydrous magnesium sulfate. Toluene was distilled off to obtain 4-formylcyclohexane carboxylic acid methyl ester 18.8 g (111 mmol). The yield was 79.2% from 4-oxocyclohexane carboxylic acid methylester.

1. dry with materialTo dried MTP 50.0 g (146 mmol), THF 500 ml
2. additionwas added
3. stirringthe mixture was stirred for 2 hours
4. extractionthe product was extracted with diethylether
5. washThe extract was washed with a sodium chloride aqueous solution
6. dry with materialdried over anhydrous magnesium sulfate
7. distillationthe solvent was distilled off
8. customThe residue was purified by silica gel column chromatography (eluent: toluene)
9. customSuch resulting
10. custompurified material
11. stirringwas stirred in mixed solvent of 2N-hydrochloric acid 500 ml and acetone 500 ml for 5 hours at room temperature
12. extractionthe product was extracted with toluene
13. washThe extract was washed with a saturated sodium bicarbonate aqueous solution
14. dry with materialwith water, and dried over anhydrous magnesium sulfate
15. distillationToluene was distilled off

ORD record

ord-84730e05557c420ab5fa64f92dd83d22

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06235355B1