Lithium Hydroxide → 4-(Hydroxymethyl)bicyclo[2.2.2]octane-1-carboxylic acid

Lithium hydroxide (2 N, 250 ml) is added to a mixture of 4-hydroxymethyl-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester (XVI, Example 91) in a mixture of THF (50 ml) and methanol (75 ml). The resulting reaction mixture is stirred at 20-25° for 16 hr, and then concentrated. The residue is diluted with water (30 ml) and washed with methylene chloride (100 ml) and ethyl acetate (100 ml). The aqueous layer is acidified with concentrated hydrochloric acid pH about 0 and extracted with ethyl acetate (3×250 ml). The ethyl acetate layers are combined and washed with saline (3×50 ml), dried over anhydrous sodium sulfate and concentrated to give the title compound, NMR (400 MHz, CDCl3) δ 3.09, 1.72 and 1.29.

1. customThe resulting reaction mixture
2. concentrationconcentrated
3. additionThe residue is diluted with water (30 ml)
4. washwashed with methylene chloride (100 ml) and ethyl acetate (100 ml)
5. extractionextracted with ethyl acetate (3×250 ml)
6. washwashed with saline (3×50 ml)
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated

ORD record

ord-a5d1efe60403438fb09f748132c97629

Source dataset

uspto-grants-2003_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06649600B1