4-Methoxybenzyl alcohol → 4-Methoxybenzaldehyde

HRID 1897550Notes

Reaction equation

HRID 1897550 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.C(N(CC)CC)C.C(N(C(C)C)CC)(C)C.CC1(C)N([O])C(C)(C)CCC1>ClCCCl>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 77384-Methoxybenzyl alcoholHCID 8471TriethylamineHCID 81531DiisopropylethylamineHCID 2724126Tempo

Product 1

HCID 312444-MethoxybenzaldehydeYield 5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The effect of the additive was then examined for the oxidation of 4-methoxybenzylalcohol using 8 (2 mol %) in 1,2-dichloroethane (Table 2). Triethylamine, diisopropylethylamine, and TEMPO were all effective promoters of the vanadium complex, affording high yields of 4-methoxybenzaldehyde after 24 h at 60° C. (Entries 2 to 5). In contrast, less than 5% yield was observed with the vanadium complex alone (no additive, Entry 1), suggesting a key role for the nitrogen base.

Workup

  1. customaffording high

Sources & evidence

ORD record
ord-bd5c66ef4f7246f08adbf502d6f29a3f
Source dataset
uspto-grants-2013_08
Patent number
US08519132B2

Reaction notes

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