Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylate → 1,4-Dioxaspiro[4.5]decan-8-ylmethanol

A 12-L, four-necked flask equipped with a mechanical stirrer, dropping funnel, thermometer and a nitrogen-inlet tube was flushed with nitrogen and then charged with a 1.0 M LAH (2754 mL, 2754 mmol). The mixture was cooled (0-4° C. internal temperature, 2-propanol/dry ice bath) and a solution of ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate (590 g, 2754 mmol) was added over 3.5 h via dropping funnel. The reaction mixture was then stirred for 3 h while allowing it to warm to room temperature then stirred for an additional 16 h at room temp. The reaction mixture was then cooled (0° C.) bath and diluted with ethyl ether (3 L). The reaction mixture was then carefully quenched by adding water (100 mL, over 1 h), followed by 15% aqueous NaOH (100 mL, over 40 min) and water (300 ml, over 30 min). After the mixture was stirred for 1 h, sodium sulfate was added and stirring continued for 10 min. The white precipitate was the filtered off and the cake was washed with ether and the filtrate concentrated to afford the title compound (440 g, 92% yield) as a light yellow liquid. Ref. J. Org. Chem. 1997, 62, 5284-5292.

1. customthermometer and a nitrogen-inlet tube was flushed with nitrogen
2. stirringthen stirred for an additional 16 h at room temp
3. temperatureThe reaction mixture was then cooled (0° C.) bath
4. customThe reaction mixture was then carefully quenched
5. additionby adding water (100 mL, over 1 h)
6. customfollowed by 15% aqueous NaOH (100 mL, over 40 min) and water (300 ml, over 30 min)
7. stirringAfter the mixture was stirred for 1 h
8. additionsodium sulfate was added
9. stirringstirring
10. waitcontinued for 10 min
11. filtrationfiltered off
12. washthe cake was washed with ether
13. concentrationthe filtrate concentrated

ORD record

ord-10259c17ddfd43f9a3d38f47c9c39ac8

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129398B2