4-Hydroxybenzaldehyde → 4-(Cyclohexylmethoxy)benzaldehyde

HRID 846257Notes

Reaction equation

HRID 846257 reaction equation
CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].[OH:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.[CH:21]1([CH2:27]Br)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>O>[CH:21]1([CH2:27][O:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 137636Cyclohexane, (bromomethyl)-

Product 1

HCID 234332874-(Cyclohexylmethoxy)benzaldehydeYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 250 ml of DMF containing about 200 g of anhydrous potassium carbonate (1.5M) was added 122 g of 4-hydroxybenzaldehyde and 177 g of cyclohexylmethylbromide. The mixture was heated to reflux temperature and maintained overnight, after which was poured into cold water and extracted with ethyl acetate. The extracts were dried and evaporated under reduced pressure to yield the desired subtitled intermediate (63% yield), b.p. 133°-138° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux temperature
  3. temperaturemaintained overnight
  4. extractionextracted with ethyl acetate
  5. customThe extracts were dried
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a79513b9d53041c6b7fba8b56ce79211
Source dataset
uspto-grants-1992_08
Patent number
US05135955

Reaction notes

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