Rac-(1r,4r)-4-methoxycyclohexane-1-carboxylic acid → (4-Methoxycyclohexyl)methanol

4-Methoxycyclohexanecarboxylic acid (7 g) in tetrahydrofuran (20 mL) was treated with 1 M (in tetrahydrofuran) borane-tetrahydrofuran complex (100 mL) overnight. The mixture was concentrated and the residue was dissolved in methanol (100 mL) and concentrated HCl (10 mL). The resulting mixture was stirred for 1 hour and concentrated. The residue was dissolved in dichloromethane and washed with water. The organic layer was dried over Na2SO4, filtered, and concentrated to give the title compound.

1. concentrationThe mixture was concentrated
2. dissolutionthe residue was dissolved in methanol (100 mL)
3. concentrationconcentrated
4. dissolutionThe residue was dissolved in dichloromethane
5. washwashed with water
6. dry with materialThe organic layer was dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-eff402b17ef648459b916d93ea1252f4

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580794B2