Water → Benzyl 4-hydroxy-2-methylbenzoate

HRID 2066399Notes

Reaction equation

HRID 2066399 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.C(=O)([O-])O.[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C)C=O>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:7])=[C:4]([CH3:11])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 684754-Hydroxy-o-toluic acidHCID 516893Potassium Bicarbonate

Product 1

HCID 18006238Benzyl 4-hydroxy-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-hydroxy-2-methylbenzoic acid (300 mg) in dimethylformamide (3 ml) was added with potassium hydrogencarbonate (236.9 mg), the mixture was stirred for 10 minutes, and then added with benzyl bromide (0.35 ml), and the mixture was stirred at 40° C. for 2 hours. The mixture was added with distilled water, the mixture was extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane to hexane ethyl acetate=50:1 to 20:1 to 2:1) to obtain the title compound (351.8 mg).

Workup

  1. stirringthe mixture was stirred at 40° C. for 2 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane to hexane ethyl acetate=50:1 to 20:1 to 2:1)

Sources & evidence

ORD record
ord-160d24bff7a7456296e02c380ac26d51
Source dataset
uspto-grants-2012_10
Patent number
US08293715B2

Reaction notes

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