Ethanol → 4-(2,3,5-Trimethylphenoxy)butanoic acid

HRID 1976294Notes

Reaction equation

HRID 1976294 reaction equation
[CH3:1][C:2]1[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([O-:10])=[O:9].[OH-].[Na+].CCO.CCOCC>O>[CH3:1][C:2]1[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9]

Participants

6

Reactant 4

HCID 702EthanolHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 220009144-(2,3,5-Trimethylphenoxy)butyrate

Product 1

HCID 144926594-(2,3,5-Trimethylphenoxy)butanoic acidYield 53.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(2,3,5-trimethylphenoxy)butyrate (9.09 g), 1N NaOH (58 ml), and EtOH (80 ml) was stirred at room temperature overnight. The reaction mixture was poured into a mixture of Et2O and water. The separated water phase was washed with Et2O, and was acidified by 6N HCl. After extraction by AcOEt, the AcOEt was washed with water and brine, and dried over MgSO4, and then evaporated. The resulting precipitate was collected by filtration, and dried to give 4-(2,3,5-trimethylphenoxy)butyric acid (4.91 g).

Workup

  1. washThe separated water phase was washed with Et2O
  2. extractionAfter extraction by AcOEt
  3. washthe AcOEt was washed with water and brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. filtrationThe resulting precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-61632a7188a643998fb8733d69e7b5f9
Source dataset
uspto-grants-2001_05
Patent number
US06225480B1

Reaction notes

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