Dimethylformamide → Benzyl 4-(hydroxymethyl)benzoate

HRID 658034Notes

Reaction equation

HRID 658034 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>O.CO>[CH2:1]([O:17][C:15](=[O:16])[C:14]1[CH:13]=[CH:12][C:11]([CH2:10][OH:9])=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 763604-(Hydroxymethyl)benzoic acid

Product 1

HCID 15650225Benzyl 4-(hydroxymethyl)benzoateYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Benzyl bromide (7.8 mL, 66 mmol) was added to a suspension of 4-hydroxymethylbenzoic acid (10 g, 66 mmol) and cesium carbonate (11 g, 33 mmol) in a mixed solvent (DMF (100 mL)-methanol (30 mL)-water (30 mL)), and then the mixture was stirred at room temperature for 2 hours. Water (500 mL) was added thereto, the whole was extracted with ethyl acetate (500 mL), and then the organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (300 mL) twice and water (300 mL) twice. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The resulting solid was collected by filtration with hexane, and dried at 35° C. under reduced pressure to give 13 g of the title reference compound as a white solid. (Yield 81%)

Workup

  1. extractionthe whole was extracted with ethyl acetate (500 mL)
  2. washthe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (300 mL) twice
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. filtrationThe resulting solid was collected by filtration with hexane
  6. customdried at 35° C. under reduced pressure
  7. customto give 13 g of the title reference compound as a white solid

Sources & evidence

ORD record
ord-6806d71095c0427cbae9528d93cbde2a
Source dataset
uspto-grants-2011_12
Patent number
US08076332B2

Reaction notes

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