Toluene → 1,4-Dioxaspiro(4.5)decane-8-carbaldehyde

Diisobutylaluminium hydride (1.5 M solution in toluene, 102 ml, 153 mmol) was added dropwise to a solution of 1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester 2 (32.13 g, 150 mmol) in absol. toluene (160 mol) at −70 to −65° C. under argon and the mixture was stirred for 30 min. The mixture was then quenched at −70 to −60° C. by addition of methanol (80 ml). The reaction solution was warmed to RT, saturated sodium chloride solution (100 ml) was added, and the reaction solution was filtered with suction over kieselguhr. The kieselguhr was washed twice with ethyl acetate, and the aqueous solution was separated and extracted twice with ethyl acetate. The combined organic extracts were washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure.

1. customThe mixture was then quenched at −70 to −60° C. by addition of methanol (80 ml)
2. additionsaturated sodium chloride solution (100 ml) was added
3. filtrationthe reaction solution was filtered with suction over kieselguhr
4. washThe kieselguhr was washed twice with ethyl acetate
5. customthe aqueous solution was separated
6. extractionextracted twice with ethyl acetate
7. washThe combined organic extracts were washed with saturated sodium chloride solution
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated under reduced pressure

ORD record

ord-3087b6126d1148d093e5f0079bfce6d9

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08124788B2