3-Benzylbenzaldehyde → 7-(3-Benzyl-phenyl)-6-heptenoic acid

HRID 2396525Notes

Reaction equation

HRID 2396525 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[C:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:19])=[O:18].CC([O-])(C)C.[K+]>C1(C)C=CC=CC=1>[CH2:1]([C:8]1[CH:9]=[C:10]([CH:11]=[CH:24][CH2:23][CH2:22][CH2:21][CH2:20][C:17]([OH:19])=[O:18])[CH:13]=[CH:14][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 131027433-BenzylbenzaldehydeHCID 18987303(6-Carboxyhexyl)triphenylphosphonium iodideHCID 23665647Potassium tert-butoxide

Product 1

HCID 538969997-(3-Benzyl-phenyl)-6-heptenoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

By using a similar procedure to that described in example 24 but with 1 g of 3-benzylbenzaldehyde, 5.5 g of (6-carboxyhexyl)triphenylphosphonium iodide, 2.5 g of potassium ter-butylate and 40 cc of toluene as the starting material (1 hour; 50° C.), and after purification by flash chromatography on silica gel (30-60 Mm; eluent: 8:2:0.05 n-hexane/ethyl acetate/acetic acid), 7-(3-benzyl-phenyl)-6-heptenoic acid is obtained. (m.p.=68° C.)

Workup

  1. customafter purification by flash chromatography on silica gel (30-60 Mm; eluent: 8:2:0.05 n-hexane/ethyl acetate/acetic acid)

Sources & evidence

ORD record
ord-03a78379e1334d7c9aed5f715da1a427
Source dataset
uspto-grants-1996_02
Patent number
US05492915

Reaction notes

Loading…