1-(p-Tolyl)cyclopropanecarboxylic acid → Methyl 1-(p-tolyl)cyclopropanecarboxylate

HRID 332679

Reaction equation

HRID 332679 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([C:7]2([C:10]([OH:12])=[O:11])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.O.[C:15]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:1]1([CH3:13])[CH:2]=[CH:3][C:4]([C:7]2([C:10]([O:12][CH3:15])=[O:11])[CH2:9][CH2:8]2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 986391-(p-Tolyl)cyclopropanecarboxylic acidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 57443305Methyl 1-(p-tolyl)cyclopropanecarboxylateYield 969.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

To a stirred solution of 1-(p-tolyl)cyclopropanecarboxylic acid (6 g, 34.05 mmol) in methanol (48 mL), was added para-toluenesulphonic acid monohydrate (0.648 g, 3.405 mmol). The reaction was stirred at 75° C. for 16 hours. The mixture was concentrated under reduced pressure, and the residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic layer was washed with saturated aqueous sodium bicarbonate solution (×2), brine and dried (magnesium sulfate), filtered, and concentrated under reduced pressure to afford the title compound as an orange oil (6.279 g, 97%). The material was used directly in the next step with no further purification.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution (×2), brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fe34e0c1a34e4020bb1a957d88d61f8d
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Linked notes

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