4-Hydroxybenzaldehyde → 4-(2-Butoxyethoxy)benzaldehyde

HRID 654414Notes

Reaction equation

HRID 654414 reaction equation
Br[CH2:2][CH2:3][O:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:5]([O:4][CH2:3][CH2:2][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1)[CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 1387612-Butoxyethyl bromide

Product 1

HCID 198872374-(2-Butoxyethoxy)benzaldehydeYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Nine grams (0.05 mole) of 1-bromo-2-butoxy-ethane and 6.1 grams (0.05 mole) of 4-hydroxybenzaldehyde were dissolved in 75 mls. of acetonitrile. Into the mixture were added 13.8 grams (0.1 mole) of finely ground potassium carbonate and the resulting reaction mixture was stirred under reflux for ten hours. The reaction mixture was allowed to cool, was filtered, washed with acetonitrile and evaporated to an amber oily product. The product was passed through a silica gel chromatographic column for recovery of a colorless oil (64% yield) having the following structure: ##STR20##

Workup

  1. customthe resulting reaction mixture
  2. temperatureunder reflux for ten hours
  3. temperatureto cool
  4. filtrationwas filtered
  5. washwashed with acetonitrile
  6. customevaporated to an amber oily product

Sources & evidence

ORD record
ord-713a336d939e408ebc21ec034e7fddc7
Source dataset
uspto-grants-1992_07
Patent number
US05132041

Reaction notes

Loading…