Dimethylformamide → Benzyl 4-hydroxy-2-methylbenzoate

HRID 484055Notes

Reaction equation

HRID 484055 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O-:12])([O-])=[O:10].[K+].[K+].CN([CH:18]=[O:19])C>CCOCC>[OH:19][C:18]1[CH:5]=[CH:4][C:3]([C:9]([O:12][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])=[C:2]([CH3:7])[CH:1]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 18006238Benzyl 4-hydroxy-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

9.5 gm (63 mmol) of material prepared as described in Step A above was dissolved in DMF (100 ml) and benzyl bromide (8.4 ml, 69.3 mmol) was added followed by powdered K2CO3 (13 gm, 94 mmol). This mixture was stirred at 60° C. for 2 hr and then was cooled, diluted with Et2O and poured onto ice chilled aq. HCl. The layers were separated and the aqueous layer was extracted twice more with Et2O. The pooled organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to dryness. This crude product was purified by flash chromatography (silica gel, using 10%-30% EtOAc in hexane as eluant) to give the title compound as an oil which upon trituration with hexane and cooling gave 8.5 gm of a white solid.

Workup

  1. temperaturewas cooled
  2. additionpoured onto ice chilled aq. HCl
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted twice more with Et2O
  5. washThe pooled organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThis crude product was purified by flash chromatography (silica gel, using 10%-30% EtOAc in hexane as eluant)

Sources & evidence

ORD record
ord-d313c23182584679a1fc6381a0af5775
Source dataset
uspto-grants-1993_07
Patent number
US05229381

Reaction notes

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