(4-Nitrophenyl)acetic acid → Methyl p-nitrophenylacetate

HRID 1807242Notes

Reaction equation

HRID 1807242 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)(Cl)=O.[CH3:18]COC(C)=O.CCCCCCC>CO>[CH3:18][O:12][C:11](=[O:13])[CH2:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 4661(4-Nitrophenyl)acetic acidHCID 24386Thionyl ChlorideHCID 21899848Ethylacetate heptane

Product 1

HCID 270191Methyl p-nitrophenylacetateYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 2-(4-nitrophenyl)acetic acid (1 g, 5.52 mmol) dissolved in methanol (100 mL) cooled to 0° C., was added thionyl chloride (1.31 mL, 11 mmol) dropwise slowly. The mixture was stirred at 0° C. for 30 min then 25° C. for 1 h. TLC Rf=0.5 PDT (50% EtOAc/heptane; Rf=0.2 for SM). The mixture was concentrated under reduced pressure to afford (4-nitro-phenyl)-acetic acid methyl ester (1.1 g, 100%). 1H NMR (CDCl3) δ 8.2 (d, 1H), 7.5 (d, 1H), 3.79 (s, 2H), 3.78 (s, 3H).

Workup

  1. wait25° C. for 1 h
  2. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-84a7c89bb7ec4782acac730f6b869fc5
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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