4-Hydroxybenzaldehyde → 4-(Cyclohexylmethoxy)benzaldehyde

HRID 1369268Notes

Reaction equation

HRID 1369268 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[OH-].[Na+]>CC#N>[CH:18]1([CH2:17][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 137636Cyclohexane, (bromomethyl)-

Product 1

HCID 234332874-(Cyclohexylmethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-hydroxybenzaldehyde (1.22 g, 10.0 mmol), K2CO3 (1.45 g, 10.5 mmol), and bromomethylcyclohexane (1.54 mL, 11.0 mmol) in CH3CN (20 mL) was stirred at reflux for three days. The reaction mixture was then cooled, poured into 1 M aq NaOH and extracted with Et2O. The extract was washed with H2O and brine. The aqueous washes were reextracted once with Et2O, and the combined extracts were dried over MgSO4 and concentrated to 2.03 g (93%) of ether as a solid. This material was used without further purification.

Workup

  1. temperatureat reflux for three days
  2. temperatureThe reaction mixture was then cooled
  3. extractionextracted with Et2O
  4. washThe extract was washed with H2O and brine
  5. dry with materialthe combined extracts were dried over MgSO4
  6. concentrationconcentrated to 2.03 g (93%) of ether as a solid
  7. customThis material was used without further purification

Sources & evidence

ORD record
ord-571acc41b2d447b4b5fda114af0531d3
Source dataset
uspto-grants-2003_06
Patent number
US06576766B1

Reaction notes

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