Hexane → 2-Pentylcyclohexa-2,5-diene-1,4-dione

HRID 1363923Notes

Reaction equation

HRID 1363923 reaction equation
[CH2:1]([C:6]1[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:7]=1[OH:8])[CH2:2][CH2:3][CH2:4][CH3:5].CCCCCC.CC(=O)OCC>CO>[CH2:1]([C:6]1[C:7](=[O:8])[CH:9]=[CH:10][C:11](=[O:13])[CH:12]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 157575732-Pentylbenzene-1,4-diol

Product 1

HCID 157575742-Pentylcyclohexa-2,5-diene-1,4-dioneYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of 360 mg (2 mmol) of 21 in methanol, 650 mg (2 eq) of FeCl3 was added. The reaction mixture was stirred for 1 hr, and the solvent was removed. Silicagel chromatography (hexane: EA=20:1) gave 210 mg (59% yield) 22 as a brown solid.

Workup

  1. customthe solvent was removed

Sources & evidence

ORD record
ord-e32effb717e54d7097d0ad9b8a24d596
Source dataset
uspto-grants-2011_02
Patent number
US07888055B2

Reaction notes

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