Water → 4-(Methoxymethyl)cyclohexan-1-one

To (1,4-dioxa-spiro[4.5]dec-8-yl)-methanol (10 g) in tetrahydrofuran (300 mL) in an ice bath was added sodium hydride (3.6 g of 60% in mineral oil) and the mixture stirred for 30 min. Methyl iodide 7.8 mL in THF (20 mL) was added dropwise and the reaction was allowed to warm slowly to room temperature overnight. Water (20 mL) was added and the reaction mixture partially concentrated, then partitioned between water (100 mL) and diethyl ether (300 mL). The organic phase was isolated, dried and concentrated in vacuo. The crude was then taken up in tetrahydrofuran (250 mL) and 40 mL of 3N aqueous HCl was added. The reaction was stirred for 2 h at room temperature, partially concentrated and then the crude product was extracted with diethyl ether, dried, concentrated and purified by flash chromatography (4 hexane: 1 ethyl acetate) to give 4-methoxymethyl-cyclohexanone 4.9 g.

1. concentrationthe reaction mixture partially concentrated
2. custompartitioned between water (100 mL) and diethyl ether (300 mL)
3. customThe organic phase was isolated
4. customdried
5. concentrationconcentrated in vacuo
6. addition40 mL of 3N aqueous HCl was added
7. stirringThe reaction was stirred for 2 h at room temperature
8. concentrationpartially concentrated
9. extractionthe crude product was extracted with diethyl ether
10. customdried
11. concentrationconcentrated
12. custompurified by flash chromatography (4 hexane: 1 ethyl acetate)

ORD record

ord-5c679ed4ebf44e5ebc58d4de50eaf4ff

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07884210B2