Methylparaben → Methyl 4-(4-phenylbutoxy)benzoate

HRID 234786Notes

Reaction equation

HRID 234786 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-].[Na+].[C:15]1([CH2:21][CH2:22][CH2:23][CH2:24]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[Na+]>CN(C=O)C>[C:15]1([CH2:21][CH2:22][CH2:23][CH2:24][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 14798Sodium HydroxideHCID 2596681-Bromo-4-phenylbutaneHCID 10942334Sodium Methoxide

Product 1

HCID 10978973Methyl 4-(4-phenylbutoxy)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of methyl 4-hydroxybenzoate (13.4 kg, 88 mol) in DMF (52 L) was added dropwise to a mixture of NaOMe (4.8 kg, 89 mol) and DMF (50 L) at room temperature under a gentle stream of nitrogen. The reaction mixture was heated at 60°-70° for 1 hr with stirring and then cooled to room temperature. To this mixture was added dropwise a solution of 4-phenylbutyl bromide (16.92 kg, 79.4 mol) in DMF (5 L). The resulting mixture was heated at 60°-70° for 1 hr with constant stirring and cooled to room temperature. After an addition of 1N-NaOH (110 L) was added, and the product was extracted twice with ethyl acetate (50 L and 80 L). The extracts were washed with 1N-NaOH (110 L) and saturated brine (20 L) successively, and then concentrated to dryness in vacuo to give the title compound in quantitative yield.

Workup

  1. temperatureThe reaction mixture was heated at 60°-70° for 1 hr
  2. temperatureThe resulting mixture was heated at 60°-70° for 1 hr
  3. stirringwith constant stirring
  4. temperaturecooled to room temperature
  5. additionwas added
  6. extractionthe product was extracted twice with ethyl acetate (50 L and 80 L)
  7. washThe extracts were washed with 1N-NaOH (110 L) and saturated brine (20 L) successively
  8. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-9a4493c5a6c941db8074fa50490c0a3b
Source dataset
uspto-grants-1997_01
Patent number
US05596103

Reaction notes

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