Water → 8-Acetyl-12-oxoheptadecanoic acid

HRID 372901Notes

Reaction equation

HRID 372901 reaction equation
[C:1]([CH:4]([CH2:14][CH2:15][CH2:16][CH:17]([OH:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])(=[O:3])[CH3:2].O.S(=O)(=O)(O)O>CC(C)=O.[O-2].[O-2].[O-2].[Cr+6]>[C:1]([CH:4]([CH2:14][CH2:15][CH2:16][C:17](=[O:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 12042400Heptadecanoic acid, 8-acetyl-12-hydroxy-

Product 1

HCID 203222718-Acetyl-12-oxoheptadecanoic acid

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolvent

Procedure

A solution of 8-acetyl-12-hydroxyheptadecanoic acid (9.85 g., 0.03 mole) in acetone (29 ml.) is cooled to 5°-10° and treated, dropwise, over 21/4 hours with a solution prepared from a mixture of chromium trioxide (2.57 g., 0.0257 mole) water (7.5 ml.) and concentrated sulfuric acid (2.1 ml.). Stirring is continued for an additional 30 minutes.

Workup

  1. additiontreated

Sources & evidence

ORD record
ord-62d28c9715ce4165964e0c9287dae71c
Source dataset
uspto-grants-1978_05
Patent number
US04092356

Reaction notes

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