4-Hydroxybenzaldehyde → 4-(6-Hydroxyhexoxy)benzaldehyde

HRID 2255840Notes

Reaction equation

HRID 2255840 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19]>C(O)C>[OH:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 14797Potassium HydroxideHCID 779706-Bromo-1-hexanol

Product 1

HCID 150510824-(6-Hydroxyhexoxy)benzaldehydeYield 55.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of potassium hydroxide (13.2 g) and 4-hydroxybenzaldehyde (20.6 g, 169 mmol) in ethanol (320 ml) was refluxed for 30 min. 6-Bromohexanol (24.5 g, 135 mmol) dissolved in ethanol (30 ml) were added and the reaction mixture was refluxed for 16 h. The solvent was then removed in vacuo. Dichloromethane (400 ml) was added no the residue. The organic layer was washed with aqueous sodium hydroxide (1 M, 300 ml), water (500 ml) and brine (250 ml), filtered, dried over anhydrous sodium sulfate and concentrated in vacuo. Recritstallisation of the residue from dichloromethane/petroleum ether yielded (13) as a pale yellow solid (16.7 g, 45%). The analytical data was in accordance with that reported by C. Noel, C. Friedrich, V. Leonard, P. LeBarney, G. Ravaux, and J. C. Dubois, Makromol. Chem., Macromol. Symp., 1989, 24, 283.

Workup

  1. additionwere added
  2. temperaturethe reaction mixture was refluxed for 16 h
  3. customThe solvent was then removed in vacuo
  4. additionDichloromethane (400 ml) was added no the residue
  5. washThe organic layer was washed with aqueous sodium hydroxide (1 M, 300 ml), water (500 ml) and brine (250 ml)
  6. filtrationfiltered
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c13cbe51f2bc493ca3e7ef644fda1692
Source dataset
uspto-grants-1997_08
Patent number
US05653914

Reaction notes

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