1-Propanol → 2-Cyclopentyloxy-benzaldehyde

HRID 429796Notes

Reaction equation

HRID 429796 reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[O:10])=[CH:5][C:4]=1O.[CH3:12][C:13](C)([O-:15])[CH3:14].[K+].[CH2:18](O)[CH2:19]C>>[CH:13]1([O:15][C:5]2[CH:4]=[CH:3][CH:8]=[CH:7][C:6]=2[CH:9]=[O:10])[CH2:14][CH2:19][CH2:18][CH2:12]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 isovanilin 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 1N 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 1N NaOH
  7. customThe ether phase was evaporated to dryness

Sources & evidence

ORD record
ord-2a86e40e6eb44b2c97dac082f4591e3a
Source dataset
uspto-grants-2001_11
Patent number
US06319928B1

Reaction notes

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