Butyl bromide → 4-Butoxy-3-methoxy-5-(prop-2-en-1-yl)benzaldehyde

HRID 36552Notes

Reaction equation

HRID 36552 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:13][CH3:14])[C:11]=1[OH:12])[CH:7]=[O:8])[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH2:23][CH2:24][CH3:25]>O>[CH2:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:13][CH3:14])[C:11]=1[O:12][CH2:22][CH2:23][CH2:24][CH3:25])[CH:7]=[O:8])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 15338063-Allyl-4-hydroxy-5-methoxy-benzaldehyde

Product 1

HCID 199370474-Butoxy-3-methoxy-5-(prop-2-en-1-yl)benzaldehydeYield 98.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-allyl-4-hydroxy-5-methoxybenzaldehyde (10.25 g, 0.053 mole), dimethylformanide (150 ml), potassium carbonate (8.29 g, 0.06 mole) and 1-bromobutane (8.22 g, 0.06 mole) was maintained at 40°-45° C. for three hours. The reaction mixture was plunged into iced water and the oil formed extracted with dichloromethane. After washing with water, drying and evaporation of the solvent, a brown oil was obtained which was passed through a bed of silica 60 to give a pale yellow oil, 3-allyl-4-butoxy-5-methoxybenzaldehyde (13 g, yield=91%).

Workup

  1. temperaturewas maintained at 40°-45° C. for three hours
  2. customthe oil formed
  3. extractionextracted with dichloromethane
  4. washAfter washing with water
  5. customdrying
  6. customevaporation of the solvent
  7. customa brown oil was obtained which

Sources & evidence

ORD record
ord-ca49a5c4293049cba9d5b77a8d90c519
Source dataset
uspto-grants-1995_05
Patent number
US05415854

Reaction notes

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