Vanillin → 4-Ethoxy-3-nitrobenzaldehyde

HRID 1175208Notes

Reaction equation

O[C:2]1C=CC(C=O)=C[C:3]=1OC.[OH:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][C:14]=1[N+:21]([O-:23])=[O:22]>>[CH2:2]([O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][C:14]=1[N+:21]([O-:23])=[O:22])[CH3:3]

Participants

Reactant 2

HCID 1183Vanillin

HCID 181694-Hydroxy-3-nitrobenzaldehyde

Product 1

HCID 14943794-Ethoxy-3-nitrobenzaldehydeYield 86%

Procedure

This example was according to Example 1, except that 4-hydroxy-3-methoxybenzaldehyde was replaced by 68.5 g 4-hydroxy-3-nitro-benzaldehyde (0.41 mol) to obtain 68.7 g 4-ethoxy-3-nitrobenzaldehyde in a yield of 86%. 1H-NMR (ppm) δ: 9.96 (1H, s; —CHO); 7.73 (1H, m; 2-ArH); 7.58 (1H, m; 6-ArH); 7.33 (1H, m; 5-ArH); 4.15 (2H, q; —CH2); 3.82 (3H, s; —OCH3); 1.53 (3H, t; —CH3). MS (m/Z): 195 (M+).

Sources & evidence

ORD record: ord-474468ecb1cb4f4fb217137a8ae0bc5d
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07838706B2

Reaction notes

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