4-Hydroxybenzaldehyde → 4-(Cyclopentyloxy)benzaldehyde

HRID 449489Notes

Reaction equation

HRID 449489 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH:10]1(Br)[CH2:14][CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.C(#N)C>[CH:10]1([O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 4875Potassium IodideHCID 8728BromocyclopentaneHCID 11430Potassium Carbonate

Product 1

HCID 31527244-(Cyclopentyloxy)benzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 4-hydroxybenzaldehyde (100 mg, 0.819 mmol), cyclopentyl bromide (176 μl, 1.64 mmol), potassium carbonate (340 mg, 2.46 mmol), acetonitrile (4 mL) and potassium iodide (136 mg, 819 μmol) was stirred at 60° C. for 18 h. The reaction was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give crude product 4-(cyclopentyloxy)benzaldehyde. This was used as crude in the following Step. Analytical LCMS (M+H)+: m/z=191.1.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d19a9e8fa1654a56ad81be43d5f1ae7c
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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