Homovanillyl alcohol → HCID 69203622, compound

HRID 2053460Notes

Reaction equation

HRID 2053460 reaction equation
[CH2:1]([OH:12])[CH2:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.O(C)[Na].Br[CH2:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CO.C1COCC1>[CH3:7][O:6][C:5]1[CH:4]=[C:3]([CH2:2][CH2:1][OH:12])[CH:11]=[CH:10][C:8]=1[O:9][CH2:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 16928Homovanillyl alcoholHCID 2596681-Bromo-4-phenylbutaneHCID 178418582HCID 178418582, compound

Product 1

HCID 69203622HCID 69203622, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of homovanillyl alcohol (10 g, 59.3 mmol) in dry methanol (140 ml), there is added 12 ml of 1N NaOCH3 in methanol. After addition of a solution of 1-bromo-4-phenylbutane (12.6 g, 59.3 mmol) in THF (10 ml) the reaction mixture is kept at reflux for 3 hours. After cooling the reaction is quenched with saturated aqueous NaHCO3 and extracted with ethyl acetate (2 times, 500 ml each). The organic layer is dried over MgSO4 and the solvent is removed by evaporation. The crude residue is then purified on silica gel using ethyl acetate/n-hexane (1/1) as mobile phase.

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureAfter cooling the reaction
  3. customis quenched with saturated aqueous NaHCO3
  4. extractionextracted with ethyl acetate (2 times, 500 ml each)
  5. dry with materialThe organic layer is dried over MgSO4
  6. customthe solvent is removed by evaporation
  7. customThe crude residue is then purified on silica gel

Sources & evidence

ORD record
ord-51cd0c2816dc44f4b05eafb67ad91eaf
Source dataset
uspto-grants-2008_02
Patent number
US07326801B2

Reaction notes

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