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ChemicalBook CAS DataBase List Cholic acid
81-25-4

Cholic acid synthesis

12synthesis methods
-

Yield:2955-27-3 80% ,81-25-4 10%

Reaction Conditions:

with sodium in propan-1-ol; for 3 h;Reflux;

Steps:

2.2.2. 3α,7β,12α-Trihydroxy-5β-cholane-24-oic acid 4

To a solution of 2.50 g (6.1 mmol) of 3α,12α-dihydroxy-7-keto-5β-cholane-24-oic acid 2 in 20 ml of anhydrous n-propanol was added 5.09 g (220.0 mmol) of sodium metal. Reaction mixture was refluxed and progress of reaction was monitored by TLC. Reaction was completed in 3 h. The reaction mixture was cooled to room temperature and gradually diluted with 20 ml of water, acidified with dilute hydrochloric acid, and extracted with (2 × 30 ml) of ethyl acetate. Organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to get residue which was further purified by column chromatography on silica gel using methanol-chloroform (5:95). Yield: 2 g (80%); Mp: 144 °C [lit.12 145 °C]; IR (KBr): 1704 (C0), 3448 (OH), 1042, 1010 cm-1;1H NMR (300 MHz, CDCl3): δ 0.69 (s, 3H, H-18), 0.91 (s, 3H, H-19), 3.51 (br m, 2H, H-3β and H-7α), 3.91(m, 1H, H-12β).

References:

Dangate, Prasad S.;Salunke, Chetan L.;Akamanchi, Krishnacharya G. [Steroids,2011,vol. 76,# 12,p. 1397 - 1399] Location in patent:experimental part

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