ChemicalBook CAS DataBase List 4α-Hydroxyadamantane-1-carboxylic acid

4α-Hydroxyadamantane-1-carboxylic acid synthesis

5synthesis methods

Product Name:4α-Hydroxyadamantane-1-carboxylic acid
CAS Number:81968-77-6
Molecular formula:C11H16O3
Molecular Weight:196.24

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Yield:81968-77-6 100%

Reaction Conditions:

with methanol;sodium tetrahydroborate at 20;Cooling with ice;

Steps:

3.1

Step 1; A stirred solution of 4-oxoadamantane-1-carboxylic acid (4.42 g, 22.8 mmol) in MeOH (100 mL) was cooled in an ice bath and NaBH₄tablets (4×1 g, 106 mmol) were added at 15 min intervals. The ice bath was allowed to melt and the mixture was stirred overnight at rt and concentrated under reduced pressure. The residue was diluted with 5% aq HCl (100 mL) and extracted with ether (2×125 mL). The combined ether extracts were dried over MgSO₄and concentrated to give 4-hydroxyadamantane-1-carboxylic acid (4.47 g, quant) as an off-white solid which was used directly.

References:

US2011/34455,2011,A1 Location in patent:Page/Page column 33