4-Hydroxybenzaldehyde → HCID 20135245, compound

HRID 579915Notes

Reaction equation

HRID 579915 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].S(C1C=CC(C)=CC=1)([O-])(=O)=O.[CH3:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C@@H:29](O)[CH3:30]>C(O)C>[CH3:23][CH:24]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 14798Sodium HydroxideHCID 85570p-ToluenesulfonateHCID 2723888(+)-2-Octanol

Product 1

HCID 20135245HCID 20135245, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

p-Hydroxy-benzaldehyde (15 g), ethanol (200 ml) and 50% NaOH (12 g) were mixed with stirring, followed by pouring in the mixture, a tosylate (26 g) derived from S-(+)-2-octanol, heating the resulting mixture under reflux for 6 hours, distilling off most of ethanol, adding 6N-HCl (100 ml), extracting with toluene, washing the toluene layer with acid, washing with alkali, washing with water to make it neutral, drying, concentrating, and further concentrating the resulting concentrate according to column chromatography with Al2O3 (40 g) to obtain oily p-(1-methylheptyloxy)benzaldehyde (13.0 g). Next, sodium boron hydride (1.0 g) was suspended in isopropyl alcohol (50 ml), followed by dropwise adding to the suspension, a solution of p-(1-methylheptyloxy)benzaldehyde obtained above in isopropyl alcohol (100 ml) so that the liquid temperature might not exceed 40° C., stirring the mixture at 60° C. for 4 hours, adding 6N-HCl (30 ml) and water (20 ml), further heating with stirring at 60° C., distilling off the solvent, extracting the residue with toluene, washing the toluene layer with acid, washing with alkali, washing with water to make it neutral, drying and concentrating to obtain raw p-(1-methylheptyloxy)benzyl alcohol (13 g), which was then heated together with thionyl chloride for 6 hours, followed by distilling off excess thionyl chloride under reduced pressure to obtain raw p-(1-methylheptyloxy)benzyl chloride (IIIb-2) (13 g), which was used, as it was, in the following reaction.

Workup

  1. additionby pouring in the mixture
  2. temperatureheating the resulting mixture
  3. temperatureunder reflux for 6 hours
  4. distillationdistilling off most of ethanol
  5. additionadding 6N-HCl (100 ml)
  6. extractionextracting with toluene
  7. washwashing the toluene layer with acid
  8. washwashing with alkali,
  9. washwashing with water
  10. customdrying
  11. concentrationconcentrating
  12. concentrationfurther concentrating the resulting
  13. concentrationconcentrate

Sources & evidence

ORD record
ord-4c2596344134464daf7ae73f488f3209
Source dataset
uspto-grants-1988_06
Patent number
US04751019

Reaction notes

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