Potassium Carbonate → HCID 86751427, compound

HRID 1489746Notes

Reaction equation

HRID 1489746 reaction equation
O[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(CBr)[CH2:16][CH2:15][CH2:14][CH2:13]1.[C:19](=O)([O-])[O-:20].[K+].[K+]>CN(C)C=O>[CH:12]1([C:2]2[C:3]([O:20][CH3:19])=[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 86751427HCID 86751427, 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; 2N) and water (2×50 mL), dried over magnesium sulfate, and evaporated to give 3-cyclopentyl-methoxy-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; 2N) and water (2×50 mL)
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-d3aed0bf28994a13a3f59c3efc9d7504
Source dataset
uspto-grants-1997_10
Patent number
US05679696

Reaction notes

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