Ethanol → Ethyl 1-(3-chloro-4-methoxyphenyl)cyclopropane-1-carboxylate

HRID 1773956Notes

Reaction equation

HRID 1773956 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:13]([OH:15])=[O:14])[CH2:12][CH2:11]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH3:16][CH2:17]O>Cl>[CH2:16]([O:14][C:13]([C:10]1([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Cl:1])[CH:3]=2)[CH2:11][CH2:12]1)=[O:15])[CH3:17]

Participants

4

Reactant 2

HCID 702EthanolHCID 591294641-(3-Chloro-4-methoxyphenyl)cyclopropane-1-carboxylic acid

Product 1

HCID 89650234Ethyl 1-(3-chloro-4-methoxyphenyl)cyclopropane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 1-(3-chloro-4-methoxy-phenyl)-cyclopropanecarboxylic acid (250 mg, 0.96 mmol, 1 eq.) in 1.25M HCl in EtOH (2.4 mL) was stirred at r.t. for 2 hours and further at 50° C. for 18 hours. The mixture was allowed to cool to r.t. and concentrated in vacuo. The residue was purified by flashmaster (column: 25 g, flow: 30 mL/min, 30 fractions of 30 mL, Heptane 100% to Heptane+20% AcOEt) to yield the title compound as a colorless oil. LC-MS 3: tR=0.91 min; [M+H]+=255.2

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flashmaster (column: 25 g, flow: 30 mL/min, 30 fractions of 30 mL, Heptane 100% to Heptane+20% AcOEt)

Sources & evidence

ORD record
ord-42f2df71b12149128d1a64c70621bb52
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

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