Water → Benzyl 2,4-dihydroxybenzoate

HRID 1729528Notes

Reaction equation

HRID 1729528 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C=O>[OH:3][C:4]1[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:5]=1[C:6]([O:8][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 14912,4-Dihydroxybenzoic AcidHCID 7498Benzyl BromideHCID 24758Sodium hydride

Product 1

HCID 7500968Benzyl 2,4-dihydroxybenzoateYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3 g (0.1 mole) of sodium hydride (80% in oil) and 50 ml of dimethylformamide (DMF), there are slowly added 15.4 g (0.1 mole) of 2,4-dihydroxybenzoic acid dissolved in 50 ml of DMF. The mixture is stirred at ambient temperature until the cessation of gaseous emission. There are then added 13.1 ml (0.1 mole) of benzyl bromide and the mixture is stirred at ambient temperature until solubilization of the reaction medium. The reaction mixture is poured into water, and extracted with ethyl ether. The organic phase is decanted, washed with water, dried on magnesium sulfate and evaporated- The residue is purified by chromatography on a silica column by eluting with dichloromethane. 19.7 g (81% yield) of the expected ester having a melting point of 94°-95° C. are recovered.

Workup

  1. stirringthe mixture is stirred at ambient temperature until solubilization of the reaction medium
  2. extractionextracted with ethyl ether
  3. customThe organic phase is decanted
  4. washwashed with water
  5. customdried on magnesium sulfate
  6. customevaporated- The residue is purified by chromatography on a silica column
  7. washby eluting with dichloromethane

Sources & evidence

ORD record
ord-911e0c3e41a5402daa2fd8781c41951a
Source dataset
uspto-grants-1994_07
Patent number
US05332856

Reaction notes

Loading…