p-Toluenesulfonic acid → Methyl 1-phenylcyclopropane-1-carboxylate

HRID 1908368Notes

Reaction equation

HRID 1908368 reaction equation
[C:1]1([C:7]2([C:10]([OH:12])=[O:11])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13]C1C=CC(S(O)(=O)=O)=CC=1.CCOC(C)=O>CO>[C:1]1([C:7]2([C:10]([O:12][CH3:13])=[O:11])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 802061-Phenylcyclopropanecarboxylic acid

Product 1

HCID 12861006Methyl 1-phenylcyclopropane-1-carboxylateYield 147.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-phenylcyclopropanecarboxylic acid (25 g, 0.15 mol) in CH3OH (200 mL) was added TsOH (3 g, 0.1 mol) at room temperature. The mixture was refluxed overnight. The solvent was evaporated under reduced pressure to give crude product, which was dissolved into EtOAc. The EtOAc layer washed with aq. sat. NaHCO3. The organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to give methyl 1-phenylcyclopropanecarboxylate (26 g, 96%), which was used directly in the next step. 1H NMR (400 MHz, CDCl3) δ 7.37-7.26 (m, 5H), 3.63 (s, 3H), 1.63-1.60 (m, 2H), 1.22-1.19 (m, 2H).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customThe solvent was evaporated under reduced pressure
  3. customto give crude product, which
  4. washThe EtOAc layer washed with aq. sat. NaHCO3
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2c086cf1b53848a2919f892a2356eb4f
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

Loading…