Benzaldehyde → HCID 20159059, compound

HRID 1073477Notes

Reaction equation

HRID 1073477 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:9](=[N:11]C1CCCCC1)C.O1CCC[CH2:19]1>>[OH:8][C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:19])[CH:9]=[NH:11]

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 8028TetrahydrofuranHCID 10964544N-cyclohexylethanimine

Product 1

HCID 20159059HCID 20159059, compound

Procedure

The direct aldol condensation also takes place by reacting the benzaldehyde derivative with the anion of an N-substituted ethylideneamine, for example ethylidenecyclohexylamine. The reaction, which is preferably carried out in the cold in an aprotic solvent, for example tetrahydrofuran, provides a β-hydroxy-β-phenylpropylideneamine which, with simultaneous dehydration and imine hydrolysis in an acidic medium, for example in dilute hydrochloric acid, gives the corresponding cinnamaldehyde (G. Wittig and A. Hesse, Org. Synth., 50, 67).

Workup

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Sources & evidence

ORD record
ord-16b47a5f06b2400192600ab322a8f425
Source dataset
uspto-grants-1990_11
Patent number
US04970077

Reaction notes

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