Water → 3-Cyclopentyloxy-4-methoxybenzaldehyde

HRID 1660517Notes

Reaction equation

HRID 1660517 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:5]([OH:6])[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH:18]1(Br)[CH2:22][CH2:21][CH2:20][CH2:19]1.O>CS(C)=O>[CH:18]1([O:6][C:5]2[CH:4]=[C:3]([CH:11]=[CH:10][C:7]=2[O:8][CH3:9])[CH:2]=[O:1])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 12127Isovanillin

Product 1

HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeYield 94%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To the solution of 15.22 g (100 mmoles) of isovanilline in 125 ml of dimethylsulphoxide, 27 g of powdered anhydrous potassium carbonate are added. The suspension is stirred at 60° C. for 30 minutes and then 12.9 ml (120 mmoles) of cyclopentyl bromide are added at 60° C. during 60 minutes. Then the suspension is stirred at the same temperature 8 hours, cooled to 25° C. and poured into 500 ml of water. The aqueous emulsion is extracted four times with 100 ml of ether. The collected ethereal phases are washed twice with 20 ml of 1 N sodium hydroxide solution, dried over anhydrous magnesium sulphate and evaporated. To the oily residue 100 ml of benzene are added and the evaporation is repeated. The remained oil is fractionally distilled in vacuo to give 20.65 g (94%) of title compound, b.p. 136°-138° C./0.01 Hgmm.

Workup

  1. stirringThen the suspension is stirred at the same temperature 8 hours
  2. temperaturecooled to 25° C.
  3. extractionThe aqueous emulsion is extracted four times with 100 ml of ether
  4. washThe collected ethereal phases are washed twice with 20 ml of 1 N sodium hydroxide solution
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customevaporated
  7. additionTo the oily residue 100 ml of benzene are added
  8. customthe evaporation
  9. distillationThe remained oil is fractionally distilled in vacuo

Sources & evidence

ORD record
ord-c0fd9c8f95a74cc2ae1c054b89dd3c9b
Source dataset
uspto-grants-1981_12
Patent number
US04308278

Reaction notes

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