Methanol → Methyl 3-(4-methylphenyl)-5-nitrobenzoate

HRID 77741Notes

Reaction equation

HRID 77741 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[C:10]([C:17]([OH:19])=[O:18])[CH:9]=2)=[CH:4][CH:3]=1.O=S(Cl)Cl.[CH3:24]O>>[CH3:24][O:18][C:17]([C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=1)=[O:19]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 532248984'-Methyl-5-nitro-[1,1'-biphenyl]-3-carboxylic acid

Product 1

HCID 57851213Methyl 3-(4-methylphenyl)-5-nitrobenzoateYield 92%

Procedure

To a solution of 4′-Methyl-5-nitro-biphenyl-3-carboxylic acid (10.00 g, 0.039 mol) in methanol was added SOCl2(5.09 g, 0.043 mol) at 0° C. The reaction mixture was allowed to warm to room temperature and was then heated to reflux for 2 hours. The solvent was removed in vacuo to afford 4′-Methyl-5-nitro-biphenyl-3-carboxylic acid methyl ester (9.72 g, 92%) as light yellow solid. MS (M+H)=273.

Workup

  1. temperaturewas then heated
  2. temperatureto reflux for 2 hours
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-237a5be14d334df48f347e46399f08b0
Source dataset
uspto-grants-2014_09
Patent number
US08841336B2

Reaction notes

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