Methylparaben → Methyl 4-(2-(benzyloxy)benzyloxy)benzoate

HRID 1106823Notes

Reaction equation

HRID 1106823 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18]([O:25][C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH2:28]Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[CH2:18]([O:25][C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH2:28][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 15142522-Benzyloxybenzylbromide

Product 1

HCID 22675491Methyl 4-(2-(benzyloxy)benzyloxy)benzoateYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 4-hydroxybenzoate in DMF (5 ml) was treated with K2CO3 (2.76, 20 mmol) and 2-benzyloxy benzyl bromide (1.52 g, 10 mmol). The reaction was stirred at ambient temperature over night. The reaction mixture was partitioned between ethyl acetate and water and the organic phase was washed well with water dried (MgSO4) and evaporated. The crude material was purified by chromatography [EtOAc:hexane] to give methyl 4-(2-(benzyloxy)benzyloxy)benzoate as a white solid (3.06 g, 88%).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washthe organic phase was washed well with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude material was purified by chromatography [EtOAc:hexane]

Sources & evidence

ORD record
ord-9a897355e93541c99b7ba88a9c5c5e7b
Source dataset
uspto-grants-2000_05
Patent number
US06057345

Reaction notes

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