Benzyl 4-Hydroxybenzoate → HCID 86587222, compound

HRID 2414690Notes

Reaction equation

HRID 2414690 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:19]=[CH:18][C:7]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[CH:6][CH:5]=1.Br[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25]>CS(C)=O>[CH2:11]([O:10][C:8](=[O:9])[C:7]1[CH:18]=[CH:19][C:4]([O:3][CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[CH:5][CH:6]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7180Benzyl 4-HydroxybenzoateHCID 14797Potassium HydroxideHCID 69385Pentane, 1-bromo-4-methyl-

Product 1

HCID 86587222HCID 86587222, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of KOH (0.74 g) in DMSO(15 ml) were added benzyl 4-hydroxybenzoate(1.5 g) and 1-bromo-4-methylpentane(2.78 ml), then the mixture was refluxed for an hour. Then the reaction mixture was partitioned between a mixture of ethyl acetate and water. The separated organic layer was washed in turn water, 20% aqueous sodium carbonate solution and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by a silica gel column chromatography eluting with a mixture of ethyl acetate and n-hexane (1:30) to give benzyl-4-isohexyloxybenzoate(1.18 g, 57.5%).

Workup

  1. temperaturethe mixture was refluxed for an hour
  2. customThen the reaction mixture was partitioned between a mixture of ethyl acetate and water
  3. washThe separated organic layer was washed in turn water
  4. dry with material20% aqueous sodium carbonate solution and brine, dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography
  7. washeluting with a mixture of ethyl acetate and n-hexane (1:30)

Sources & evidence

ORD record
ord-0d3a0e49057d4711a5a1d2ea6d0c8336
Source dataset
uspto-grants-2004_11
Patent number
US06812235B2

Reaction notes

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