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

HRID 1654552Notes

Reaction equation

HRID 1654552 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Cl[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[OH:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 748286-Chloro-1-hexanol

Product 1

HCID 150510824-(6-Hydroxyhexoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

2.44 g (0.02 mol) of 4-hydroxybenzaldehyde, 2.73 g (0.02 mol) of 6-chlorohexanol, 1.66 g (0.012 mol) of potassium carbonate and 20 ml of N,N-dimethylformamide were put in a three-neck 50 ml-flask equipped with a stirrer and a thermometer and heated at 100° C. for 2 hours with stirring. The reaction mixture was cooled to room temperature, poured into water containing ice and extracted with ethyl acetate. The resulting extract was dried with anhydrous sodium sulfate, and ethyl acetate was removed therefrom by distillation. The oily residue was allowed to stand at room temperature, whereupon it gradually crystallized. By silica gel thin layer chromatography (using a developer of ethyl acetate), the purity of the crystals was high. The yield of the product was 4.4 g (99.0%).

Workup

  1. custom50 ml-flask equipped with a stirrer
  2. temperatureThe reaction mixture was cooled to room temperature
  3. additioncontaining ice
  4. extractionextracted with ethyl acetate
  5. extractionThe resulting extract
  6. dry with materialwas dried with anhydrous sodium sulfate, and ethyl acetate
  7. customwas removed
  8. distillationby distillation
  9. customto stand at room temperature, whereupon it
  10. customgradually crystallized

Sources & evidence

ORD record
ord-bae6eb3f9ee34a86b3740ed70cb32abd
Source dataset
uspto-grants-1995_04
Patent number
US05408009

Reaction notes

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