Benzyl Bromide → Methyl 2-hydroxy-3-propyl-4-benzyloxybenzoate

HRID 2289087Notes

Reaction equation

HRID 2289087 reaction equation
[OH:1][C:2]1[C:11]([CH2:12][CH2:13][CH3:14])=[C:10]([OH:15])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[OH:1][C:2]1[C:11]([CH2:12][CH2:13][CH3:14])=[C:10]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 13019281Methyl 2,4-dihydroxy-3-propylbenzoate

Product 1

HCID 18701907Methyl 2-hydroxy-3-propyl-4-benzyloxybenzoate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of methyl 2,4-dihydroxy-3-propylbenzoate (3.00 grams) in 2-butanone (30 mL) was treated with benzyl bromide (1.70 mL) and potassium carbonate (1.972 grams). The mixture was refluxed for 4 hours. The reaction mixture was partitioned between isopropyl acetate and pH 4 buffer. The organic was washed once with water, then dried over magnesium sulfate. The organic was filtered and evaporated to an oil which was chromatographed over silica gel to afford the title compound.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. customThe reaction mixture was partitioned between isopropyl acetate and pH 4 buffer
  3. washThe organic was washed once with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe organic was filtered
  6. customevaporated to an oil which
  7. customwas chromatographed over silica gel

Sources & evidence

ORD record
ord-900c89412cd34dd0b52e12659f399e85
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Reaction notes

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