1-Propanol → 2-Cyclopentyloxy-benzaldehyde

HRID 1585557Notes

Reaction equation

HRID 1585557 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:7](OC)=[C:5](O)[CH:4]=1.C[C:13]([CH3:16])([O-:15])[CH3:14].[K+].[CH2:18](O)[CH2:19]C>>[CH:13]1([O:15][C:4]2[CH:5]=[CH:7][CH:10]=[CH:11][C:3]=2[CH:2]=[O:1])[CH2:16][CH2:19][CH2:18][CH2:14]1

Participants

4

Reactant 3

HCID 10311-PropanolHCID 12127IsovanillinHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 31527232-Cyclopentyloxy-benzaldehydeYield 77.5%

Procedure

77.70 g (500 mmoles) of isovanillin and 69.40 g (600 mmoles) of 97% potassium t-butoxide (t-BuOK) dissolved in 800 ml of 1-propanol, 69.0 ml 630 mmoles), and the solution refluxed. After 3 hours another 9.25 g (80 mmoles) of t-BuOK were added at 80° C. and the suspension refluxed for another 3 hours. The solid was filtered off and the filtrate evaporated in vacuo to dryness. The residue was dissolved in ether and extracted with IN NaOH. The ether phase was evaporated to dryness: 85.40 g (77.5%) of cyclopentyloxybenzaldehyde was isolated.

Workup

  1. temperature69.0 ml 630 mmoles), and the solution refluxed
  2. temperaturethe suspension refluxed for another 3 hours
  3. filtrationThe solid was filtered off
  4. customthe filtrate evaporated in vacuo to dryness
  5. dissolutionThe residue was dissolved in ether
  6. extractionextracted with IN NaOH
  7. customThe ether phase was evaporated to dryness

Sources & evidence

ORD record
ord-3ed661963d4d4676aa5d421bfc66bcea
Source dataset
uspto-grants-1999_08
Patent number
US05939422

Reaction notes

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