1-Bromopropane → Ethyl 4-propoxybenzoate

HRID 497509Notes

Reaction equation

HRID 497509 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.Br[CH2:14][CH2:15][CH3:16].[H-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH2:9]([O:8][C:6](=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:14][CH2:15][CH3:16])=[CH:12][CH:11]=1)[CH3:10]

Participants

6

Reactant 3

HCID 78401-BromopropaneHCID 8434EthylparabenHCID 24758Sodium hydride

Product 1

HCID 22750767Ethyl 4-propoxybenzoateYield 91%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(Scheme 1, Compound A) To a solution of ethyl 4-hydroxybenzoate (2.0 g, 12 mmol) and bromopropane (4.0 g, 32.8 mmol) in DMF (50 mL) was added NaH (60% in mineral oil, 0.80 g, 20.8 mmol). The resultant suspension was stirred at room temperature for 1.0 hour. The mixture was diluted with ethyl acetate (EtOAc) (300 mL), washed with H2O, and then was dried over Na2SO4. After filtration and concentration in vacuo, the residue was purified by flash chromatography (SiO2: EtOAc/Hexanes). This compound was obtained as a yellow oil (2.26 g, 10.9 mmol, 91% yield). 1H NMR (DMSO-d6) δ 7.89 (d, 2H, J=8.7 Hz), 7.00 (d, 2H, J=9.0 Hz), 4.24 (q, 2H, J=6.9 Hz), 3.98 (t, 2H, J=6.6 Hz), 1.72 (m, 2H), 1.29 (t, 3H, J=6.6 Hz), 0.97 (t, 3H, J=7.2 Hz); Anal. Calcd for C12H16O3.0.47C6H14: C, 71.54; H, 9.14; N, 0.00. Found: C, 71.57; H, 8.78; N, 0.00; Mass Spec.: 209.04 (MH+).

Workup

  1. washwashed with H2O
  2. dry with materialwas dried over Na2SO4
  3. filtrationAfter filtration and concentration in vacuo
  4. customthe residue was purified by flash chromatography (SiO2: EtOAc/Hexanes)

Sources & evidence

ORD record
ord-8197aed50777412abb7c1d35d041ca93
Source dataset
uspto-grants-2005_09
Patent number
US06949574B2

Reaction notes

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