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

HRID 1006026Notes

Reaction equation

HRID 1006026 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-0adbe506be154123990211a141842074
Source dataset
uspto-grants-2004_09
Patent number
US06787562B2

Reaction notes

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