Bromocyclopentane → 3-Cyclopentyloxy-4-methoxybenzaldehyde

HRID 1940291Notes

Reaction equation

HRID 1940291 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].[H-].[Na+].[CH:14]1(Br)[CH2:18][CH2:17][CH2:16][CH2:15]1>CN(C)C=O.O>[CH:14]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])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 8728BromocyclopentaneHCID 12127IsovanillinHCID 24758Sodium hydride

Product 1

HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A stirred solution of 3-hydroxy-4-methoxybenzaldehyde (2.00 g) in dry dimethylformamide (20 mL) is treated portionwise with sodium hydride (60% dispersion in oil; 0.56 g) and the mixture is then heated for 1 hour at 50° C. It is then treated dropwise with cyclopentyl bromide (2.36 g) and is stirred and heated at 50° C. for 22 hours. The solution is diluted with water (100 mL) and extracted with diethyl ether (2×100 mL). The ethereal extracts are combined, dried over magnesium sulfate and concentrated, to give 3-cyclopentyloxy-4-methoxybenzaldehyde (1.65 g) in the form of a golden oil.

Workup

  1. temperatureheated at 50° C. for 22 hours
  2. extractionextracted with diethyl ether (2×100 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4e8a7ebbf6144490a64603fb03defc5b
Source dataset
uspto-grants-1997_12
Patent number
US05698711

Reaction notes

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