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

HRID 1255540Notes

Reaction equation

HRID 1255540 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 1,995.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(4-methoxy-phenyl)-cyclopropanecarboxylic acid (50.0 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 was 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 (53.5 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 (m, 2H), 1.15 (m, 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 was 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-39f15d9780bc4164be39994b28e6bb69
Source dataset
uspto-grants-2013_06
Patent number
US08461156B2

Reaction notes

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