1-Propanol → 2-(Cyclopentyloxy)benzaldehyde

반응식

[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

참가 물질

반응물 3

HCID 10311-Propanol

HCID 12127Isovanillin

HCID 23665647Potassium tert-butoxide2회

생성물 1

HCID 31527232-(Cyclopentyloxy)benzaldehyde수율 77.5%

실험 절차

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.