Acetic Anhydride → HCID 7107477, compound

HRID 1462318Notes

Reaction equation

HRID 1462318 reaction equation
[CH3:1][C@@H:2]([C@@H:8]1[C@@:12]2([CH3:27])[CH2:13][CH2:14][C@@H:15]3[C@@:20]4([CH3:26])[CH2:21][CH2:22][C@@H:23]([OH:25])[CH2:24][C@H:19]4[CH2:18][CH2:17][C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[C:28](OC(=O)C)(=[O:30])C>Cl(O)(=O)(=O)=O.C(O)=O>[CH:28]([O:25][C@@H:23]1[CH2:22][CH2:21][C@@:20]2([CH3:26])[C@H:19]([CH2:18][CH2:17][C@@H:16]3[C@@H:15]2[CH2:14][CH2:13][C@@:12]2([CH3:27])[C@H:11]3[CH2:10][CH2:9][C@@H:8]2[C@H:2]([CH3:1])[CH2:3][CH2:4][C:5]([OH:7])=[O:6])[CH2:24]1)=[O:30]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 9903Lithocholic Acid

Product 1

HCID 7107477HCID 7107477, compound

Reagents, catalysts & solvents 2

HCID 24247Perchloric AcidCatalystHCID 284Formic AcidSolvent

Conditions

Temperature
40 °C

Procedure

Ten grams of lithocholic acid was dissolved in 40 ml. of 89.9% formic acid and 8 drops of 70% perchloric acid, and the resulting solution heated to 55° C. with stirring. The solution was then cooled to 40° C. at which time 35 ml. of acetic anhydride was slowly added and the temperature of the reaction mixture maintained between 55°-60° C. The solution was cooled and poured into 500 ml. of water and the resulting precipitate was filtered, washed with water and dried to yield 3α-formyloxy-5β-cholan-24-oic acid.

Workup

  1. temperaturethe temperature of the reaction mixture maintained between 55°-60° C
  2. temperatureThe solution was cooled
  3. additionpoured into 500 ml
  4. filtrationof water and the resulting precipitate was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-2da859e3d6c84900a817ecc8526a111e
Source dataset
uspto-grants-1984_07
Patent number
US04460509

Reaction notes

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