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

HRID 344632Notes

Reaction equation

HRID 344632 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].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][CH2:28][CH2:29][CH3:30]>O>[CH2:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:13][CH3:14])[C:11]=1[O:12][CH2:27][CH2:28][CH2:29][CH3:30])[CH:7]=[O:8])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 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 3-allyl-4-hydroxy-5-methoxybenzaldehyde (10.25 g, 0.053 mole), of dimethylformamide (150 ml), of potassium carbonate (8.29 g, 0.06 mole) and of 1-bromobutane (8.22 g, 0.06 mole) was maintained at 40°-45° C. for 3 hours. The reaction mixture was dropped into iced water and the oil formed was extracted with dichloromethane. After washing with water, drying and evaporating off the solvent, a brown oil was obtained, which was passed through a bed of silica 60 to give a pale yellow oil of 3-allyl-4-butoxy-5-methoxybenzaldehyde (13 g, yield=91%).

Workup

  1. customthe oil formed
  2. extractionwas extracted with dichloromethane
  3. washAfter washing with water
  4. customdrying
  5. customevaporating off the solvent
  6. customa brown oil was obtained

Sources & evidence

ORD record
ord-c11fa96cb6b44ad1b71ac53162d8d152
Source dataset
uspto-grants-1991_10
Patent number
US05053290

Reaction notes

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