Orcinol → 4-(6-Isopropenyl-3-methylcyclohex-2-enyl)-5-methylbenzene-1,3-diol

HRID 2238621Notes

Reaction equation

HRID 2238621 reaction equation
[CH3:1][C:2]1(O)[CH2:7][CH2:6][C@@H:5]([C:8]([CH3:10])=[CH2:9])[CH:4]=[CH:3]1.[CH3:12][C:13]1[CH:14]=[C:15]([OH:20])[CH:16]=[C:17]([CH:19]=1)[OH:18].O.O.C(O)(=O)C(O)=O>C1(C)C=CC=CC=1.C(OCC)C>[C:8]([CH:5]1[CH:4]([C:14]2[C:13]([CH3:12])=[CH:19][C:17]([OH:18])=[CH:16][C:15]=2[OH:20])[CH:3]=[C:2]([CH3:1])[CH2:7][CH2:6]1)([CH3:10])=[CH2:9]

Participants

6

Reactant 3

HCID 10436OrcinolHCID 61373Oxalic acid dihydrateHCID 11528376(4R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-2-enol

Product 1

HCID 115797634-(6-Isopropenyl-3-methylcyclohex-2-enyl)-5-methylbenzene-1,3-diolYield 154.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

(4R)-1-Methyl-4-isopropenylcyclohex-2-ene-1-ol (300 mg, 2 mmoles) was dissolved in toluene (20 ml) and 5-methylresorcinol (248 mg, 2 mmoles) was added in diethyl ether (5 ml). Oxalic acid dihydrate (252 mg, 2 mmoles) was added and the reaction mixture heated with stirring at 80° for 5 hours. The reaction mixture was allowed to cool and diluted with diethyl ether (30 ml). The ether solution washed twice with aqueous sodium bicarbonate and dried over anhydrous magnesium sulphate. The solvents were evaporated under reduced pressure to give the crude product as a brown oil (800 mg). The product was purified using a silica column eluted with ethyl acetate:isohexane 1:9 going to ethyl acetate:isohexane 2:8.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto cool
  3. washThe ether solution washed twice with aqueous sodium bicarbonate
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customThe solvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-4e3623d018654d249526194f1ebd623b
Source dataset
uspto-grants-2010_05
Patent number
US07718830B2

Reaction notes

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