Water → HCID 11249146, compound

HRID 1199316Notes

Reaction equation

HRID 1199316 reaction equation
[C:1]([O:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:12]([CH2:13][CH:14]=[C:15]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C@@:16]43[O:37][C@H:17]4[CH2:18][C@@H:19]2[C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl(O)(=O)(=O)=O.O>CC(C)=O>[C:1]([O:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:12]([CH2:13][CH2:14][C:15]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C:16]=3[C:17](=[O:37])[CH2:18][C@@H:19]2[C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24247Perchloric Acid2×HCID 14696446HCID 14696446, compound

Product 1

HCID 11249146HCID 11249146, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
26 °C

Procedure

A stirred mixture of 28.4 kg (3β,5α,15α)-14,15-epoxycholest-7-en-3-ol benzoate (3) (Example 2) in 280 liters of acetone, under nitrogen, in a 200gallon reactor, at 22° C. was treated with 100 ml of 70% perchloric acid. The mild exothermic reaction raised the reaction mixture temperature to 26° C. in about a 5 minute period The mixture was cooled to 21° C. and an additional 180 ml of 70% perchloric acid was added. The reaction mixture temperature was kept at 22±1° C. and the mixture was stirred for 3 hours to complete the reaction. The mixture was cooled and treated with 140 liters of water at 19° C. for 30 minutes, then stirred 20 minutes more. The solid was collected by filtration, washed with a large quantity of water and dried in vacuo at 40°-60° C. to give 29.3 kg of the desired crude product (6).

Workup

  1. customThe mild exothermic reaction
  2. temperaturewas cooled to 21° C.
  3. customwas kept at 22±1° C.
  4. customthe reaction
  5. temperatureThe mixture was cooled
  6. stirringstirred 20 minutes more
  7. filtrationThe solid was collected by filtration
  8. washwashed with a large quantity of water
  9. customdried in vacuo at 40°-60° C.

Sources & evidence

ORD record
ord-8665dbe5a7d6489099aebf880b65ed5b
Source dataset
uspto-grants-1990_02
Patent number
US04900477

Reaction notes

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