Water → 3-Cyclopentyloxy-4-methoxybenzaldehyde

HRID 1058997Notes

Reaction equation

HRID 1058997 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(Br)[CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH:12]1([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

6

Reactant 4

HCID 962WaterHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 12127Isovanillin

Product 1

HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 3-hydroxy-4-methoxybenzaldehyde (30 g, 0.2 mol), cyclopentyl bromide (35.77 g, 0.24 mol) and potassium carbonate (38.6 g, 0.28 mol) in N,N-dimethylformamide (200 ml) was stirred vigorously for three days. Water (300 ml) was added and the mixture was extracted four times with ethyl acetate. The combined organic extract was washed three times with 10% aqueous sodium hydroxide solution, once with water, once with brine, dried (sodium sulfate) and evaporated to provide the title compound as a clear orange oil (36.47 g, 83%). 1H-NMR (400 MHz, CDCl3): δ 9.84 (s, 1H), 7.43 (dd, 1H, J=8.3 Hz, 1.8 Hz), 7.39 (d, 1H, J=1.8 Hz), 6.96 (d, 1H, J=8.3 Hz), 4.86 (m, 1H), 3.93 (s, 3H), 2.0 (m, 2H), 1.8-1.95 (m, 4H), 1.63 (m, 2H)

Workup

  1. extractionthe mixture was extracted four times with ethyl acetate
  2. extractionThe combined organic extract
  3. washwas washed three times with 10% aqueous sodium hydroxide solution
  4. dry with materialonce with water, once with brine, dried (sodium sulfate)
  5. customevaporated

Sources & evidence

ORD record
ord-d7210d00dd004ade85b091346418fc37
Source dataset
uspto-grants-2003_02
Patent number
US06518306B1

Reaction notes

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