Sodium Hydroxide → 4-Cyclopropyl-2-methylbenzoic acid

HRID 2245726Notes

Reaction equation

HRID 2245726 reaction equation
[CH:1]1([C:4]2[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[C:6]([CH3:14])[CH:5]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([C:4]2[CH:13]=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[C:6]([CH3:14])[CH:5]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59020660Methyl 4-cyclopropyl-2-methylbenzoate

Product 1

HCID 590206584-Cyclopropyl-2-methylbenzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-cyclopropyl-2-methylbenzoate (32.00 g, 168 mmol), 250 mL of 5 M aqueous sodium hydroxide, and 150 mL of methanol were stirred at 85° for 18 hr. Cooled the reaction mixture to room temperature and concentrated in vacuo. Dissolved the white residue in 500 mL of water, cooled the solution in an ice bath, and added 120 mL of concentrated hydrochloric acid. A white precipitate formed. Extracted the aqueous mixture with 2×250 mL EtOAc. Combined the organic extracts and washed with 250 mL brine. Dried the solution over MgSO4 and concentrated in vacuo to obtain 4-cyclopropyl-2-methylbenzoic acid as an off-white solid (29.52 g, 168 mmol). MS (ESI) MS (ESI) 175.0 (M−H)−.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionDissolved the white residue in 500 mL of water
  3. temperaturecooled the solution in an ice bath
  4. additionadded 120 mL of concentrated hydrochloric acid
  5. customA white precipitate formed
  6. extractionExtracted the aqueous mixture with 2×250 mL EtOAc
  7. washwashed with 250 mL brine
  8. dry with materialDried the solution over MgSO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-df4eee790a384fb48de5c8be65a64943
Source dataset
uspto-grants-2010_03
Patent number
US07683064B2

Reaction notes

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