1-Propanol → 2-Cyclopentyloxy-benzaldehyde

HRID 1597298Notes

Reaction equation

HRID 1597298 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 refined 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. filtrationThe solid was filtered off
  3. customthe filtrate evaporated in vacuo to dryness
  4. dissolutionThe residue was dissolved in ether
  5. extractionextracted with 1N NaOH
  6. customThe ether phase was evaporated to dryness

Sources & evidence

ORD record
ord-bec6ffbb5c1c4e3d9cd950fda28d4013
Source dataset
uspto-grants-2001_09
Patent number
US06294541B1

Reaction notes

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