1-(4-Methoxyphenyl)cyclopropane-1-carboxylic acid → Methyl 1-(4-methoxyphenyl)-cyclopropanecarboxylate

HRID 503230Notes

Reaction equation

HRID 503230 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:12]([OH:14])=[O:13])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.O.[C:16]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:16][O:13][C:12]([C:9]1([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH2:10][CH2:11]1)=[O:14]

Participants

4

Reactant 2

HCID 855751-(4-Methoxyphenyl)cyclopropane-1-carboxylic acidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 13707544Methyl 1-(4-methoxyphenyl)-cyclopropanecarboxylateYield 1,976.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(4-methoxy-phenyl)-cyclopropanecarboxylic acid (50 g, 0.26 mol) in MeOH (500 mL) was added toluene-4-sulfonic acid monohydrate (2.5 g, 13 mmol) at room temperature. The reaction mixture was heated at reflux for 20 hours. MeOH was removed by evaporation under vacuum and EtOAc (200 mL) was added. The organic layer washed with sat. aq. NaHCO3 (100 mL) and brine, dried over anhydrous Na2SO4 and evaporated under vacuum to give 1-(4-methoxy-phenyl)-cyclopropanecarboxylic acid methyl ester (53 g, 99%). 1H NMR (CDCl3, 400 MHz) δ 7.25-7.27 (m, 2H), 6.85 (d, J=8.8 Hz, 2H), 3.80 (s, 3H), 3.62 (s, 3H), 1.58 (q, J=3.6 Hz, 2H), 1.15 (q, J=3.6 Hz, 2H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 20 hours
  3. customMeOH was removed by evaporation under vacuum and EtOAc (200 mL)
  4. additionwas added
  5. washThe organic layer washed with sat. aq. NaHCO3 (100 mL) and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-583d035eb4494e8a9b00ea9eb89b10db
Source dataset
uspto-grants-2010_08
Patent number
US07776905B2

Reaction notes

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