Orcinol → HCID 86615879, compound

HRID 2427776Notes

Reaction equation

HRID 2427776 reaction equation
[CH3:1][C:2]1(O)[CH2:7][CH2:6][C@H:5]([CH:8]=[CH:9][C:10](=[CH2:12])[CH3:11])[CH:4]=[CH:3]1.[CH3:14][C:15]1[CH:16]=[C:17]([OH:22])[CH:18]=[C:19]([CH:21]=1)[OH:20].O.O.C(O)(=O)C(O)=O>C1(C)C=CC=CC=1.C(OCC)C>[CH3:14][C:15]1[C:16]([CH:4]2[CH:5]([CH:8]=[CH:9][C:10](=[CH2:11])[CH3:12])[CH2:6][CH2:7][C:2]([CH3:1])=[CH:3]2)=[C:17]([OH:22])[CH:18]=[C:19]([OH:20])[CH:21]=1

Participants

6

Reactant 3

HCID 10436OrcinolHCID 61373Oxalic acid dihydrateHCID 86615880HCID 86615880, compound

Product 1

HCID 86615879HCID 86615879, compoundYield 140.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

(4R)-1-Methyl-4-isoprenylcyclohex-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.

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

Sources & evidence

ORD record
ord-39ff9a53457e414db8d83c5604bd5226
Source dataset
uspto-grants-2011_06
Patent number
US07968711B2

Reaction notes

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