Acetone → HCID 12790678, compound

HRID 1076757Notes

Reaction equation

HRID 1076757 reaction equation
[CH3:1][C:2]1[C:3](=[O:19])[C:4]([CH2:11][CH2:12][CH:13]([CH3:18])[CH2:14][CH2:15][CH2:16][OH:17])=[C:5]([CH3:10])[C:6](=[O:9])[C:7]=1[CH3:8].[CH3:20][C:21](C)=O.S(=O)(=O)(O)[OH:25]>O.[O-2].[O-2].[O-2].[Cr+6]>[CH3:10][C:5]1[C:6](=[O:9])[C:7]2[C:2]([C:3](=[O:19])[C:4]=1[CH2:11][CH2:12][CH:13]([CH3:18])[CH2:14][CH2:15][C:16]([OH:25])=[O:17])=[CH:1][CH:21]=[CH:20][CH:8]=2

Participants

6

Reactant 3

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 21538228HCID 21538228, compound

Product 1

HCID 12790678HCID 12790678, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent2×

Procedure

To 0.05 part of 2,3,5-trimethyl-6-(6'-hydroxy-3'-methylhexyl)-1,4-benzoquinone (Formula (III) wherein R=H3C) obtained in Reference Example 4 in 300 volume parts of acetone is added, at 0°C, 10 volume parts of solution prepared by dissolving 267 parts of chromium trioxide in 230 volume parts of 98 % sulfuric acid and diluting the solution with water to make a total of 1000 volume parts. The mixture is stirred for 10 minutes and, following the dilution with 2000 volume parts of water extracted with 300 volume parts of diethyl ether. The solvent is distilled off and the residue is recrystallized from ligroine. The described procedure gives 0.05 part of 2,3,5-trimethyl-6-(5'-carboxy-3'-methylpentyl)-1,4-benzoquinone (Formula (I), wherein R=H3C; Z=H) as yellowish needles melting at 58°C-61°C.

Workup

  1. additionis added, at 0°C
  2. custom10 volume parts of solution prepared
  3. extractionextracted with 300 volume parts of diethyl ether
  4. distillationThe solvent is distilled off
  5. customthe residue is recrystallized from ligroine

Sources & evidence

ORD record
ord-90a22153d2f946e7a0c21c7777e561db
Source dataset
uspto-grants-1976_05
Patent number
US03957836

Reaction notes

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