Water → Benzyl 2,4-dihydroxybenzoate

HRID 2256346Notes

Reaction equation

HRID 2256346 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C=O)C>[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:5]

Participants

6

Reactant 4

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

Product 1

HCID 7500968Benzyl 2,4-dihydroxybenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

15.4 g (0.1 mol) of 2,4-dihydroxybenzoic acid dissolved in 50 ml of DMF are added dropwise to a solution of 3 g (0.1 mol) of sodium hydride (80% in oil) and 50 ml of DMF and the mixture is stirred at room temperature until evolution of gas has ceased. 13.1 ml (0.1 mol) of benzyl bromide are then added and the mixture is stirred at room temperature until the reaction mixture has dissolved. The reaction mixture is poured into water and extracted with ethyl ether, and the organic phase is separated, washed with water, dried over magnesium sulphate and evaporated. The residue is purified by chromatography on a silica column, eluting with dichloromethane. 19.7 g (81%) of the expected ester are collected, which melts at 94°-95° C.

Workup

  1. stirringthe mixture is stirred at room temperature until the reaction mixture
  2. dissolutionhas dissolved
  3. extractionextracted with ethyl ether
  4. customthe organic phase is separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customThe residue is purified by chromatography on a silica column
  9. washeluting with dichloromethane
  10. custom19.7 g (81%) of the expected ester are collected

Sources & evidence

ORD record
ord-8a87ad9a24d048d3883ce78c04965275
Source dataset
uspto-grants-1997_08
Patent number
US05654331

Reaction notes

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