3-Chloro-4-ethoxybenzaldehyde → 3-Chloro-4-propoxybenzoic acid

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][CH3:13])[CH:5]=[O:6].ClC1C=C(C=CC=1OCC)C=[O:19]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][CH3:13])[C:5]([OH:19])=[O:6]

Participants

Reactant 2

HCID 47700353-Chloro-4-ethoxybenzaldehyde

HCID 47728213-Chloro-4-propoxybenzaldehyde

Product 1

HCID 87071503-Chloro-4-propoxybenzoic acidYield 95%

Procedure

When the product of Step B was substituted for 3-chloro-4-ethoxybenzaldehyde in Example 49, Step A the identical process afforded the title compound in 95% yield, as a colourless solid. 1H-NMR (CDCl3) 1.00 (tr, 3H, J=7.38 Hz); 1.73-1.87 (m, 2H); 3.98 (tr, 2H, J=6.47 Hz); 6.85 (d, 1H, J=8.65 Hz); 7.84 (dd, 1H, J=2.09, 8.68 Hz); 7.98 (d, 1H, J=2.07 Hz).

Sources & evidence

ORD record: ord-4158b4fdd91a4aaca1999b52999c8aa5
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Reaction notes

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