2-Phenoxybenzoic acid → o-Phenoxybenzaldehyde

HRID 863581Notes

Reaction equation

HRID 863581 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O(C1C=CC=CC=1C(O)=O)C1C=CC=CC=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 752372-Phenoxybenzoic acidHCID 2724130Cornforth reagentHCID 36601112-Phenoxybenzyl alcoholHCID 68718528lithium aluminium hydride THF

Product 1

HCID 88060o-PhenoxybenzaldehydeYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-phenoxybenzyl alcohol (4.0 g, 20.2 mmol, prepared by the reduction of commercially available 2-phenoxybenzoic acid with LiAlH4 /THF) and 150 mL CH2Cl2 was treated with pyridinium dichromate (11.39 g, 30.3 mmol) at 25° C. and stirred for another 36 hours. The mixture was filtered through d.e. and then through a pad of silica gel to produce 3.11 g (78%) of title compound as a yellow oil. 1H NMR (CDCl3) δ6.8 (d, 1H), 6.9 (d, 1H), 7.0 (m, 2H), 7.1 (m, 2H), 7.2 (m, 1H), 8.9 (m, 1H), 10.2 (s, 1H).

Workup

  1. filtrationThe mixture was filtered through d.e

Sources & evidence

ORD record
ord-404ef53e5420495e896d2796b7bf052d
Source dataset
uspto-grants-1998_02
Patent number
US05721255

Reaction notes

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