4-Hydroxybenzaldehyde → 4-(3-Phenylpropoxy)benzaldehyde

HRID 1739399Notes

Reaction equation

HRID 1739399 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[C:12]1([CH2:18][CH2:19][CH2:20]Br)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C=O)C>[C:12]1([CH2:18][CH2:19][CH2:20][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 12503(3-Bromopropyl)benzeneHCID 24758Sodium hydride

Product 1

HCID 211912554-(3-Phenylpropoxy)benzaldehydeYield 94.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.77 g of 4-hydroxybenzaldehyde were dissolved in 30 ml of DMF, and 0.95 g of 60% NaH were further added to the resultant solution. The solution was then stirred for 1 hour after elevating the temperature of the solution up to room temperature. After cooling the solution with ice, 4.3 g of 3-phenyl-1-bromopropane were fed dropwise thereto and the solution was then further stirred for 1 hour at room temperature and subsequently for a night at 50-60° C. The solution reacted was poured into ice-water, extracted with ethyl acetate, then the organic layer resulted was dried with anhydrous magnesium sulfate. Then, the solvent used was distillated under reduce pressure, and the residue obtained was purified by using silica gel column chromatography, for which a mixture of hexane and ethyl acetate (mixing ratio, 4:1) was used for the developer, thereby affording 4.9 g of 4-(3-phenylpropyloxy)benzaldehyde.

Workup

  1. customup to room temperature
  2. stirringthe solution was then further stirred for 1 hour at room temperature and subsequently for a night at 50-60° C
  3. customThe solution reacted
  4. extractionextracted with ethyl acetate
  5. customthe organic layer resulted
  6. dry with materialwas dried with anhydrous magnesium sulfate
  7. customthe residue obtained
  8. customwas purified
  9. additionfor which a mixture of hexane and ethyl acetate (mixing ratio, 4:1)

Sources & evidence

ORD record
ord-565109f5e8b84a279a4398f3e00add90
Source dataset
uspto-grants-1999_10
Patent number
US05965743

Reaction notes

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