Benzoyl chloride → HCID 86738596, compound

HRID 223448Notes

Reaction equation

HRID 223448 reaction equation
[OH:1][C@@H:2]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@H:4]([C@@H:5]([OH:27])[CH2:6][C@@H:7]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:17])[CH2:13][CH2:14][CH:15]=[O:16])[CH2:3]1.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>N1C=CC=CC=1>[C:28]([O:1][C@@H:2]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@H:4]([C@@H:5]([O:27][C:5](=[O:27])[C:4]3[CH:22]=[CH:23][CH:24]=[CH:2][CH:3]=3)[CH2:6][C@@H:7]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:17])[CH2:13][CH2:14][CH:15]=[O:16])[CH2:3]1)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 86738597HCID 86738597, compound

Product 1

HCID 86738596HCID 86738596, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

One gram of 3α,6α-bis(hydroxy)-5α-cholane-24-al is dissolved in 5 ml of pyridine. With external cooling, 1 ml of benzoyl chloride is added dropwise with stirring. The mixture is kept at room temperature for five hours, then stirred with ice water. By extraction with methylene chloride, the reaction product is removed. The methylene chloride solution is repeatedly washed with dilute hydrochloric acid, then with water. After drying, the solvent is evaporated. The residue is 3α,6α-bis(benzoyloxy)-5α-cholane-24-al.

Workup

  1. extractionBy extraction with methylene chloride
  2. customthe reaction product is removed
  3. washThe methylene chloride solution is repeatedly washed with dilute hydrochloric acid
  4. customAfter drying
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-3ed4553553ac4008a093c0ce638f29fe
Source dataset
uspto-grants-1982_10
Patent number
US04354972

Reaction notes

Loading…