Hydrochloric Acid → Methyl cholate

HRID 1973707Notes

Reaction equation

HRID 1973707 reaction equation
[CH3:1][C@@H:2]([C@@H:8]1[C@@:12]2([CH3:29])[C@@H:13]([OH:28])[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][C@@H:17]([OH:27])[C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].Cl.[CH3:31]O>>[CH3:1][C@@H:2]([C@@H:8]1[C@@:12]2([CH3:29])[C@@H:13]([OH:28])[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][C@@H:17]([OH:27])[C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH2:3][CH2:4][C:5]([O:7][CH3:31])=[O:6]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 221493Cholic Acid

Product 1

HCID 10960835Methyl cholate

Procedure

A mixture of 100 g cholic acid, 300 ml of methanol and 10 ml concentrated hydrochloric acid was refluxed on steam for 20 minutes. The resulting brown solution was refrigerated to induce crystallization. The crystals were collected, washed with 50 ml cold methanol, and dried to give 103 g methyl cholate, m.p. 153-154° C.

Workup

  1. temperaturewas refluxed on steam for 20 minutes
  2. customcrystallization
  3. customThe crystals were collected
  4. washwashed with 50 ml cold methanol
  5. customdried

Sources & evidence

ORD record
ord-7c0580c3e4df4985a41b4e4922b9e33f
Source dataset
uspto-grants-1976_12
Patent number
US03998859

Reaction notes

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