Benzaldehyde → Stilbene

HRID 885080Notes

Reaction equation

HRID 885080 reaction equation
C1(OC=O)C=CC=CC=1.[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH:18]1[CH:23]=[C:22](Cl)[CH:21]=[C:20]([C:25](OO)=O)[CH:19]=1.[Br-]>>[C:11]1([CH:10]=[CH:25][C:20]2[CH:21]=[CH:22][CH:23]=[CH:18][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 4

HCID 240BenzaldehydeHCID 259Bromide ionHCID 70297m-Chloroperbenzoic acidHCID 74626Phenyl formate

Product 1

HCID 11502Stilbene

Procedure

Formic acid phenyl ester 7 may be synthesized from the corresponding benzaldehyde via traditional oxidation methods known in the art. For example, Baeyer-Villiger oxidation using m-CPBA to form 7, followed by deformylation using a suitable base and exposure to bromide 8 affords stilbene analog 9.

Workup

  1. customto form 7

Sources & evidence

ORD record
ord-8069c601c35046bd880d04d0ef6b285e
Source dataset
uspto-grants-2012_08
Patent number
US08242144B2

Reaction notes

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