1-Bromopropane → 3-Methoxy-2-propoxybenzaldehyde

HRID 1362041Notes

Reaction equation

HRID 1362041 reaction equation
[OH:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Br[CH2:13][CH2:14][CH3:15].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:11][O:10][C:9]1[C:2]([O:1][CH2:13][CH2:14][CH3:15])=[C:3]([CH:6]=[CH:7][CH:8]=1)[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 8991o-VanillinHCID 11430Potassium Carbonate

Product 1

HCID 31593253-Methoxy-2-propoxybenzaldehydeYield 101.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 2-hydroxy-3-methoxy-benzaldehyde (10.0 g, 65.6 mmol), 1-bromopropane (60 mL, 657 mmol) and K2CO3 (11.3 g, 82.1 mmol) in MeCN (250 mL) was heated to reflux for 12 h. The mixture was cooled to ambient temperature and the solution filtered. The filtrate was concentrated to give the title compound (12.9 g, quantitative) as light yellow oil: MS (ESI) m/e 195 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 h
  3. filtrationthe solution filtered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3d86034fbccf44f2bdca28b78c57b601
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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