Potassium Carbonate → HCID 21716330, compound

HRID 1383546Notes

Reaction equation

HRID 1383546 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[CH:12]1([CH2:17]Br)[CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:12]1([CH2:17][O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=2[O:10][CH3:11])[CH:5]=[O:6])[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12127IsovanillinHCID 12723264(Bromomethyl)cyclopentane

Product 1

HCID 21716330HCID 21716330, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred solution of 3-hydroxy-4-methoxy-benzaldehyde (5.74 g) in dry dimethylformamide (50 mL) is treated with cyclopentylmethyl bromide (7.34 g) and potassium carbonate (15 g), and the solution is heated at 60° C. for 24 hours. After cooling and filtration, the solution is evaporated to low bulk and dissolved in ethyl acetate (100 mL). The organic solution is washed with aqueous sodium hydroxide solution (4×50 mL; 2 N) and water (2×50 mL), dried over magnesium sulfate, and evaporated to give 3-cyclopentylmethoxy-4-methoxybenzaldehyde (6.5 g) in the form of a light brown oil.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltration
  3. customthe solution is evaporated to low bulk
  4. dissolutiondissolved in ethyl acetate (100 mL)
  5. washThe organic solution is washed with aqueous sodium hydroxide solution (4×50 mL; 2 N) and water (2×50 mL)
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-7018785340974f7baaf81773ce8a3f9f
Source dataset
uspto-grants-2001_07
Patent number
US06255326B1

Reaction notes

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