4-Hydroxybenzaldehyde → HCID 178444467, compound

HRID 2371348Notes

Reaction equation

HRID 2371348 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10]([C@H:15]1[CH2:20][CH2:19][C@H:18]([CH2:21][CH2:22][CH2:23]Br)[CH2:17][CH2:16]1)[CH2:11][CH2:12][CH2:13][CH3:14].C(=O)([O-])[O-].[K+].[K+].CC(=O)CC>O>[CH2:10]([C@H:15]1[CH2:20][CH2:19][C@H:18]([CH2:21][CH2:22][CH2:23][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:17][CH2:16]1)[CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 178444432HCID 178444432, compound

Product 1

HCID 178444467HCID 178444467, compoundYield 121.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.9 g of 4-hydroxybenzaldehyde, 5.0 g of 3-(trans-4-pentylcyclohexyl)-1-propyl bromide, 8.3 g of potassium carbonate and 50 ml of butanone was heated under reflux overnight. Subsequently, the cooled reaction mixture was poured into water and extracted three times with 50 ml of diethyl ether each time. The combined organic phases were washed with 500 ml of water, dried over magnesium sulphate, filtered and concentrated. Chromatography of the residue on silica gel with toluene and recrystallization from ethanol gave 6.0 g of pure 4-[3-(trans-4-pentylcyclohexyl)-1-propyloxy]benzaldehyde.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customSubsequently, the cooled reaction mixture
  4. extractionextracted three times with 50 ml of diethyl ether each time
  5. washThe combined organic phases were washed with 500 ml of water
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customChromatography of the residue on silica gel with toluene and recrystallization from ethanol

Sources & evidence

ORD record
ord-d6749063ee40420fa34bbe6a5a7bf53b
Source dataset
uspto-grants-1992_03
Patent number
US05093027

Reaction notes

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