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

HRID 990023Notes

Reaction equation

HRID 990023 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-ada549b18d5d4d8e838eb93ca885be70
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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