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

HRID 1966009Notes

Reaction equation

HRID 1966009 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 20.5%

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 was 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. The product was isolated as a yellow gum (106 mg)

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto cool
  3. washThe ether solution was washed twice with aqueous sodium bicarbonate
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customThe solvents were evaporated under reduced pressure
  6. customto give the crude product as a brown oil (800 mg)
  7. customThe product was purified
  8. washeluted with ethyl acetate:isohexane 1:9 going to ethyl acetate:isohexane 2:8

Sources & evidence

ORD record
ord-467c76166c7a4115a26d22fdfb1575d4
Source dataset
uspto-grants-2013_04
Patent number
US08420637B2

Reaction notes

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