4-Hydroxybenzaldehyde → 4-(Cyclohexylmethoxy)benzaldehyde

HRID 846255Notes

Reaction equation

HRID 846255 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH:10]1([CH2:16]Br)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.CO.C(=O)([O-])[O-].[K+].[K+]>O>[CH:10]1([CH2:16][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 887MethanolHCID 11430Potassium CarbonateHCID 137636Cyclohexane, (bromomethyl)-

Product 1

HCID 234332874-(Cyclohexylmethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Hydroxybenzaldehyde (244 g) and 354 g of cyclohexylmethylbromide were added to 1 liter of methanol containing 414 g of anhydrous potassium carbonate (3.0M). The mixture was heated to reflux temperature overnight after which it was poured into cold water and extracted with ethyl acetate. The extracts were dried and evaporated in vacuo to yield the desired subtitled intermediate.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux temperature overnight after which it
  3. extractionextracted with ethyl acetate
  4. customThe extracts were dried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-1fe4b536f4e843a6bfea6b6d7654c0bd
Source dataset
uspto-grants-1992_08
Patent number
US05135955

Reaction notes

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