Dimethylformamide → 6-Hydroxy-2,3-dimethoxybenzaldehyde

HRID 485177Notes

Reaction equation

HRID 485177 reaction equation
O1CCCCC1[O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1.C1([Li])C=CC=CC=1.CN(C)[CH:27]=[O:28]>>[CH3:17][O:16][C:10]1[C:11]([O:14][CH3:15])=[CH:12][CH:13]=[C:8]([OH:7])[C:9]=1[CH:27]=[O:28]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 202715542-(3,4-Dimethoxyphenoxy)oxaneHCID 178506676HCID 178506676, compound

Product 1

HCID 130921156-Hydroxy-2,3-dimethoxybenzaldehyde

Procedure

3,4-Dimethoxyphenol tetrahydropyranyl ether (47.6 g, 0.2 M) was lithiated with phenyllithium (from 21.02 ml bromobenzene and 2.89 g lithium), formylated by the addition of dry dimethylformamide (15 ml) and subsequently hydrolysed in an analogous manner to that described in example 2(E). The crude product was distilled under high vacuum to give 2,3-dimethoxy-6-hydroxybenzaldehyde as a yellow oil which solidified on standing. After trituration with 40/60 petrol and filtration the product had m.p. 53°-54° C. (Found: C, 59.18; H, 5.54. C9H10O4 requires C, 59.33; H, 5.53%). (C) 5-(2-Formyl-3-hydroxy-4-methoxyphenoxy)pentanoic acid

Workup

  1. distillationThe crude product was distilled under high vacuum

Sources & evidence

ORD record
ord-8c6a11c0ea624c8ba7b86073ea8f5dba
Source dataset
uspto-grants-1985_08
Patent number
US04535183

Reaction notes

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