Vanillin → 4-Cyclopentyloxy-3-methoxy-benzaldehyde

HRID 378971Notes

Reaction equation

HRID 378971 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[CH:12]1(Br)[CH2:16][CH2:15][CH2:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.O.O>[CH:12]1([O:9][C:8]2[CH:10]=[CH:11][C:3]([CH:2]=[O:1])=[CH:4][C:5]=2[O:6][CH3:7])[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

7

Reactant 3

HCID 1183VanillinHCID 8728BromocyclopentaneHCID 11430Potassium Carbonate

Product 1

HCID 31527214-Cyclopentyloxy-3-methoxy-benzaldehydeYield 97%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of vanillin (10 g, 65.7 mmoles), cyclopentyl bromide (21.09 g, 196.7 mmoles), tetrabutylammonium bromide (211.8 mg, 0.675 mmoles) and K2CO3 (27.16 g, 199.48 mmoles) in tetrahydrofuran/water 8:2 (200 ml) was refluxed under nitrogen and vigorous stirring for 55 hours, then diluted with water, extracted with ethyl acetate, and the extract was washed with water, anhydrified over Na2SO4 and dried to give an oil which was purified by silica gel flash chromatography (eluent: petrolatum/ethyl acetate 9:1) and gave 14 g of the title product (yield: 97%).

Workup

  1. temperaturewas refluxed under nitrogen
  2. extractionextracted with ethyl acetate
  3. washthe extract was washed with water
  4. customdried
  5. customto give an oil which
  6. customwas purified by silica gel flash chromatography (eluent: petrolatum/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-09ae0d75bff744368e7bffeff31bb43a
Source dataset
uspto-grants-2001_10
Patent number
US06297257B1

Reaction notes

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