Bromocyclopentane → 3-Cyclopentyloxy-4-methoxybenzaldehyde

HRID 976658Notes

Reaction equation

HRID 976658 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]1(Br)[CH2:11][CH2:10][CH2:9][CH2:8]1.[O:13]=[CH:14][C:15]1[CH:23]=[CH:22][C:19]([O:20][CH3:21])=[C:17]([OH:18])[CH:16]=1>CN(C)C=O.O>[CH:7]1([O:18][C:17]2[CH:16]=[C:15]([CH:23]=[CH:22][C:19]=2[O:20][CH3:21])[CH:14]=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 12127Isovanillin

Product 1

HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeYield 73.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (27.6 g, 0.20 mole) was added to a solution of cyclopentyl bromide (26.4 g, 0.18 mole) and isovanillin (25.8 g, 0.17 mole) in N,N-dimethyl formamide (80 mL). The resulting suspension was stirred at ambient temperature for 1 week, then diluted with water (about 500 mL) and extracted with diethyl ether (2×300 mL). The combined ether extracts were washed with water (5×150 mL), 10% sodium hydroxide (3×50 mL), and water (2×100 mL), then dried over magnesium sulfate and concentrated under vacuum to provide 27.5 g of 3-cyclopentyloxy-4-methoxybenzaldehyde as a viscous yellow oil.

Workup

  1. extractionextracted with diethyl ether (2×300 mL)
  2. washThe combined ether extracts were washed with water (5×150 mL), 10% sodium hydroxide (3×50 mL), and water (2×100 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2e1ba7b7df134999b70ecffae47bb5c3
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Reaction notes

Loading…