Methylparaben → Methyl 4-[(4-methoxyphenyl)methoxy]benzoate

HRID 858190Notes

Reaction equation

HRID 858190 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.CC(C)([O-])C.[K+].[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1>CN(C=O)C>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:24][C:23]2[CH:26]=[CH:27][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 699934-Methyloxybenzyl chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 12648420Methyl 4-[(4-methoxyphenyl)methoxy]benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4-hydoxybenzoate (6.85 g, 45 mmole) in 80 ml DMF was added potassium tert. butoxide (5.6 g, 51 mmole) and the mixture was stirred at room temperature for one hour. 4-Methoxybenzyl chloride (8.3 g, 52 mmole) was added and the mixture was stirred overnight at room temperature. The mixture was evaporated under reduced pressure and 200 ml ethyl acetate was added. The organic phase was washed four times with water, dried with sodium sulfate and evaporated under reduced pressure. Yield: 12.3 g=100%

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. customThe mixture was evaporated under reduced pressure and 200 ml ethyl acetate
  3. additionwas added
  4. washThe organic phase was washed four times with water
  5. dry with materialdried with sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d6ca1b57ab794e74b45c679a557a6831
Source dataset
uspto-grants-2006_12
Patent number
US07148243B2

Reaction notes

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