Bromocyclopentane → 3-Cyclopentyloxy-4-methoxybenzaldehyde

HRID 975236Notes

Reaction equation

HRID 975236 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].C(=O)([O-])[O-].[K+].[K+].[CH:18]1(Br)[CH2:22][CH2:21][CH2:20][CH2:19]1>CN(C)C=O>[CH:18]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])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 12127Isovanillin

Product 1

HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeYield 94.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
55 °C

Procedure

To a stirred solution of 3-hydroxy-4-methoxybenzaldehyde (140 g; 0.92 mol) in dimethylformamide (700 ml) was added dry potassium carbonate (2.54 g; 1.84 mol). The mixture was neared to 55° C. and cyclopentyl bromide (74 g; 1.97 ml; 1.84 mol) in dimethylformamide (300 ml) was added dropwise over 2 hours. After complete addition, the mixture was stirred at 55° C. for 15 hours, cooled, filtered and the solvent removed in vacuo. The residue was dissolved in CH2Cl2 and washed with 1.0M NaOH to eliminate any trace of phenol. The organic layer was dried (MgSO4) and purified by column chromatography (SiO2 ; CH2Cl2). The solution was concentrated in vacuo to give the title compound as an oil (192 g). δH (CDCl3) 1.5-2.0 (8H, br m, (CH2)4), 3,87 (3H, s, OMe), 4.80 (1H, br m, OCHCH2), 6.90 (1H, d, J 8.7 Hz, ArH ortho to OMe), 7.30-7.45 (2H, m, 2×ArH meta to OMe) and 9.77 (1H. s, ArCHO)

Workup

  1. customwas neared to 55° C.
  2. additionAfter complete addition
  3. temperaturecooled
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. dissolutionThe residue was dissolved in CH2Cl2
  7. washwashed with 1.0M NaOH
  8. dry with materialThe organic layer was dried (MgSO4)
  9. custompurified by column chromatography (SiO2 ; CH2Cl2)
  10. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-836276185f7e4c498b0c3dbb31605aa8
Source dataset
uspto-grants-1997_03
Patent number
US05608070

Reaction notes

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