Potassium Nitrate → 1-(4-Nitro-phenyl)-cyclopropanecarboxylic acid methyl ester

HRID 1908369Notes

Reaction equation

[C:1]1([C:7]2([C:10]([O-:12])=[O:11])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:13]([O-:16])([O-])=[O:14].[K+].OS(O)(=O)=O.[CH2:23](Cl)Cl>>[N+:13]([C:4]1[CH:5]=[CH:6][C:1]([C:7]2([C:10]([O:12][CH3:23])=[O:11])[CH2:9][CH2:8]2)=[CH:2][CH:3]=1)([O-:16])=[O:14]

Participants

Reactant 3

HCID 24434Potassium Nitrate

HCID 69314111-Phenylcyclopropanecarboxylate

HCID 86615737H2SO4 CH2Cl2

Product 1

HCID 591294291-(4-Nitro-phenyl)-cyclopropanecarboxylic acid methyl esterYield 68%

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-phenylcyclopropanecarboxylate (20.62 g, 0.14 mol) in H2SO4/CH2Cl2 (40 mL/40 mL) was added KNO3 (12.8 g, 0.13 mol) in portion at 0° C. The mixture was stirred for 0.5 hr at 0° C. Ice water was added and the mixture was extracted with EtOAc (100 mL×3). The organic layers were dried with anhydrous Na2SO4 and evaporated to give methyl 1-(4-nitrophenyl)cyclopropanecarboxylate (21 g, 68%), which was used directly in the next step. 1H NMR (300 MHz, CDCl3) δ 8.18 (dd, J=2.1, 6.9 Hz, 2H), 7.51 (dd, J=2.1, 6.9 Hz, 2H), 3.64 (s, 3H), 1.72-1.69 (m, 2H), 1.25-1.22 (m, 2H).

Workup

extractionthe mixture was extracted with EtOAc (100 mL×3)
dry with materialThe organic layers were dried with anhydrous Na2SO4
customevaporated

Sources & evidence

ORD record: ord-576bf9ed709c4b23abb3794336676264
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598181B2

Reaction notes

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