3-Methylbenzeneethanol → 4-Nitro-3-(2-m-tolyl-ethoxy)-benzoic acid methyl ester

Reaction equation

[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([OH:13])[CH:5]=1.[CH3:15][C:16]1[CH:17]=[C:18]([CH2:22][CH2:23]O)[CH:19]=[CH:20][CH:21]=1>>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([O:13][CH2:23][CH2:22][C:18]2[CH:17]=[C:16]([CH3:15])[CH:21]=[CH:20][CH:19]=2)[CH:5]=1

Participants

Reactant 2

HCID 746483-Methylbenzeneethanol

HCID 294866Methyl 3-hydroxy-4-nitrobenzoate

Product 1

HCID 670764364-Nitro-3-(2-m-tolyl-ethoxy)-benzoic acid methyl esterYield 86.9%

Procedure

3-Hydroxy-4-nitro-benzoic acid methyl ester (1.00 g, 5.07 mmol) and 2-(3-methylphenyl)-ethanol (0.829 g, 6.09 mmol) were reacted in analogy to step 1 of example 1 to give 1.39 g of the title compound.

Sources & evidence

ORD record: ord-245f82be1c0044ecaeff642b3d0cb5e6
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802720B2

Reaction notes

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