Phosphoric Acid → Retinoic Acid

HRID 1033960Notes

Reaction equation

[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:21])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:20])=[CH:17]/[CH:18]=[O:19].CC(=CC)C.Cl([O-])=[O:28].[Na+].P(=O)(O)(O)O>O1CCOCC1>[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:8])([CH3:9])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:21])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:20])=[CH:17]/[C:18]([OH:28])=[O:19]

Participants

Conditions

Temperature: 5 °C

Procedure

A 200-ml three-necked flask was charged under an atmosphere of nitrogen with 8.86 g of vitamin A aldehyde (80.1% purity, 25 mmoles, ratio of 13-cis form: 92%), 50 g of 2-methyl-2-butene, 20 ml of dioxane and 10 g of a 25% aqueous sodium chlorite solution, and the mixture was mechanically stirred vigorously. Then, 32 g of an aqueous phosphoric acid solution was added dropwise thereto, while the internal temperature was maintained at 5° C., over 15 minutes. Vigorous stirring was continued at 5° C. for further 40 minutes. Confirmation of completion of the reaction and after-treatment were conducted in the same manner as in Example 1, to obtain 3.46 g of vitamin A acid with a purity of at least 99%. The yield was 46%. The vitamin A acid thus obtained had a 13-cis form ratio of 95%.

Workup

customConfirmation of completion of the reaction

Sources & evidence

ORD record: ord-04928a4a025549859f584d15d18be310
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05312978

Reaction notes

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