1,3-Dibromopropane → 4-Methoxy-3-(3-methoxypropoxy)benzenemethanol

HRID 2258292Notes

Reaction equation

HRID 2258292 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][CH2:10]Br.[OH:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH:16]=[O:17]>C(#N)C>[CH3:22][O:21][C:20]1[CH:19]=[CH:18][C:15]([CH2:16][OH:17])=[CH:14][C:13]=1[O:12][CH2:8][CH2:9][CH2:10][O:4][CH3:1]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 12127Isovanillin

Product 1

HCID 451081634-Methoxy-3-(3-methoxypropoxy)benzenemethanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (272.3 g) and 1,3-dibromopropane (1.34 liters) are added to a solution of 3-hydroxy-4-methoxy-benzaldehyde (200 g) in acetonitrile and the white suspension is stirred under reflux for 19 hours. After cooling, the mixture is filtered, the solvent and excess 1,3-dibromopropane are removed under reduced pressure and the residue is purified by FC on silica gel (ethyl acetatelhexane 1:3). The title compound is obtained in the form of a white solid (334 g): Rf (ethyl acetate/hexane 1:1)=0.50. Anal. C11H13BrO3 (273.13): calc. C, 48.37; H, 4.80; Br, 29.26; found C, 48.61; H, 4.84; Br, 29.19.

Workup

  1. temperatureunder reflux for 19 hours
  2. temperatureAfter cooling
  3. filtrationthe mixture is filtered
  4. customthe solvent and excess 1,3-dibromopropane are removed under reduced pressure
  5. customthe residue is purified by FC on silica gel (ethyl acetatelhexane 1:3)

Sources & evidence

ORD record
ord-76152c43ef014a9c974cdccb029ba6c6
Source dataset
uspto-grants-1997_08
Patent number
US05659065

Reaction notes

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