Dichloromethane → 2,2,2-Trichloroethyl 4-(2,3,5-trimethylphenoxy)butyrate

HRID 1976295Notes

Reaction equation

HRID 1976295 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]([OH:10])=[O:9].[Cl:17][C:18]([Cl:22])([Cl:21])[CH2:19]O.Cl.CN(C)CCCC(N=C=N)C.C(Cl)Cl>O.CCOC(C)=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]([O:10][CH2:19][C:18]([Cl:22])([Cl:21])[Cl:17])=[O:9]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8259TrichloroethanolHCID 144926594-(2,3,5-Trimethylphenoxy)butanoic acidHCID 219829211-(3-Dimethylaminopropyl)ethylcarbodiimide hydrochloride

Product 1

HCID 220009152,2,2-Trichloroethyl 4-(2,3,5-trimethylphenoxy)butyrate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(2,3,5-trimethylphenoxy)butyric acid (4.82 mg) dimethylaminopyridine (DMAP, 0.26 g), 2,2,2-trichloroethanol (2.50 ml), 1-(3-dimethylaminopropyl)ethylcarbodiimide hydrochloride (4.57 g) and CH2Cl2 was stirred at room temperature overnight. The reaction mixture was poured into a mixture of AcOEt and water. The separated AcOEt was washed with dil. HCl, sat. NaHCO3, water, and brine, and dried over MgSO4, and then evaporated to give 2,2,2-trichloroethyl 4-(2,3,5-trimethylphenoxy)butyrate (8.11 g) as an oil compound.

Workup

  1. washThe separated AcOEt was washed with dil. HCl, sat. NaHCO3, water, and brine
  2. dry with materialdried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-b6296ef4325640a78ae35397a2d59229
Source dataset
uspto-grants-2001_05
Patent number
US06225480B1

Reaction notes

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