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

HRID 355785Notes

Reaction equation

HRID 355785 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-3029f14e6faa4648baabac54d905ba88
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

Loading…