Sodium Hydroxide → 3-chloro-4-(2-methylpropyl)Benzoic acid

HRID 2189748Notes

Reaction equation

HRID 2189748 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH2:13][CH:14]([CH3:16])[CH3:15])[C:5]([O:7]CC)=[O:6].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH2:13][CH:14]([CH3:16])[CH3:15])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59316731Ethyl 3-chloro-4-(2-methylpropyl)benzoate

Product 1

HCID 593167203-chloro-4-(2-methylpropyl)Benzoic acidYield 86.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 3-chloro-4-(2-methylpropyl)benzoate (D17) (1.76 g, 7.33 mmol), and aqueous sodium hydroxide (2M, 3.70 mL, 7.4 mmol) in ethanol (30 mL) was heated at 40° C. for 3 h. The reaction mixture was concentrated in vacuo and the residue partitioned between ethyl acetate (100 mL) and water (100 mL), the latter acidified with 2M HCl (4 mL). The aqueous layer was extracted with ethyl acetate (100 mL) and the combined organic extracts dried (phase separator) and concentrated in vacuo to give the title compound as a white solid (1.35 g, 6.36 mmol). MS (ES): C11H1335ClO2 requires 212; found 211 (M−H+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between ethyl acetate (100 mL) and water (100 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (100 mL)
  4. customthe combined organic extracts dried (phase separator)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-27fdfcaaff0a48a8be8c909b0c6adf57
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

Loading…