Hydrochloric Acid → 2-Methyl-4-(1-methyl-cyclopropyl)-benzoic acid

HRID 2069784Notes

Reaction equation

HRID 2069784 reaction equation
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH3:13])[CH2:12][CH2:11]2)=[CH:6][C:5]=1[CH3:14].CO.[OH-].[Na+].Cl>O>[CH3:14][C:5]1[CH:6]=[C:7]([C:10]2([CH3:13])[CH2:12][CH2:11]2)[CH:8]=[CH:9][C:4]=1[C:3]([OH:15])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 592165062-Methyl-4-(1-methyl-cyclopropyl)-benzoic acid methyl ester

Product 1

HCID 592164362-Methyl-4-(1-methyl-cyclopropyl)-benzoic acidYield 85.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

2-Methyl-4-(1-methyl-cyclopropyl)-benzoic acid methyl ester (2.75 g, 13.46 mmol) was treated with methanol and 5 M aqueous sodium hydroxide solution (20.46 ml, 102.32 mmol). This solution was heated to 80° C. for 4 hours. The reaction mixture was concentrated until methanol was evaporated. A white solid was obtained. The solid was dissolved in 50 ml water under heating then cooled with an ice bath; acidified with 10 ml conc. hydrochloric acid. A white precipitate was formed; filtered; washed with water; dried under high vacuum over night to yield 2-Methyl-4-(1-methyl-cyclopropyl)-benzoic acid (2.18 g, 11.46 mmol) MS (ESI) 189.1 (M-H)−

Workup

  1. concentrationThe reaction mixture was concentrated until methanol
  2. customwas evaporated
  3. customA white solid was obtained
  4. temperatureunder heating
  5. temperaturethen cooled with an ice bath
  6. customA white precipitate was formed
  7. filtrationfiltered
  8. washwashed with water
  9. customdried under high vacuum over night

Sources & evidence

ORD record
ord-d35a44d663af4f76b434c62867d443c7
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

Loading…