Potassium Hydroxide → Isotretinoin

HRID 567391

Reaction equation

HRID 567391 reaction equation
C[C@H]1[C@](C[CH2:11][C:12]2[C:16](=O)[O:15][CH:14]([OH:18])[CH:13]=2)(C)C(=C)C=CC1.[CH3:19][C:20]1[CH2:25][CH2:24][CH2:23][C:22]([CH3:27])([CH3:26])[C:21]=1/[CH:28]=[CH:29]/[C:30](O)([CH:32]=[CH2:33])[CH3:31].Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[K+]>C(O)C.O>[CH3:19][C:20]1[CH2:25][CH2:24][CH2:23][C:22]([CH3:27])([CH3:26])[C:21]=1/[CH:28]=[CH:29]/[C:30](/[CH3:31])=[CH:32]/[CH:33]=[CH:11]/[C:12](/[CH3:16])=[CH:13]\[C:14]([OH:18])=[O:15]

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 64368461,4-Pentadien-3-ol, 3-methyl-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-HCID 12196763TriphenylphosphinehydrochlorideHCID 21773091Hydroxy butenolide

Product 1

HCID 5282379Isotretinoin

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

43 g of the mixture of retinoic acids from the condensation of hydroxy butenolide, vinyl beta-ionol and triphenylphosphine hydrochloride in 10 ml of ethanol are treated with 15 g of a 50% potassium hydroxide aqueous solution, subsequently diluted to 200 mL with water, added with 30 mg of Bengal rose, then irradiated with a 18 Watt lamp for 12 hours.

Workup

  1. additionadded with 30 mg of Bengal
  2. customirradiated with a 18 Watt lamp for 12 hours

Sources & evidence

ORD record
ord-53c33f094f89499a89ea20c9541d821d
Source dataset
uspto-grants-2001_01
Patent number
US06177579B1

Linked notes

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