Sodium Iodide → Ethyl 4-(3,4-dichlorophenoxy)butanoate

HRID 1715343Notes

Reaction equation

HRID 1715343 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[Cl:9][C:10]1[CH:11]=[C:12]([OH:17])[CH:13]=[CH:14][C:15]=1[Cl:16].[CH2:18]([O:20][C:21](=[O:26])[CH2:22][CH2:23][CH2:24]Br)[CH3:19].[OH-].[Na+]>CC(C)=O.CCOC(C)=O.CCCCCC>[CH2:18]([O:20][C:21](=[O:26])[CH2:22][CH2:23][CH2:24][O:17][C:12]1[CH:13]=[CH:14][C:15]([Cl:16])=[C:10]([Cl:9])[CH:11]=1)[CH3:19]

Participants

9

Reactant 5

HCID 5238Sodium IodideHCID 72583,4-DichlorophenolHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 21812850Ethyl 4-(3,4-dichlorophenoxy)butanoate

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 8058HexaneSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

Potassium carbonate (27.5 mmol, 3.75 g) and sodium iodide (0.3333 mmol, 0.0500 g) were added to a reaction mixture of 3,4-dichloro-phenol Compound 16a (30.25 mmol, 4.93 g) and 4-bromo-butyric acid ethyl ester Compound 16b (27.5 mmol, 5.36 g) in acetone (60 mL). The reaction mixture was stirred overnight at room temperature. TLC analysis (4:1 hexane:EtOAc) showed no formation of product. The reaction mixture was refluxed for 3 hrs and TLC analysis (4:1 hexane:EtOAc) showed trace of starting material Compound 16a. The reaction mixture was refluxed overnight, then basified with 1N NaOH solution and extracted with CH2Cl2. The organics were dried over MgSO4. The drying agent was filtered and the solvent was removed in vacuo to yield 4-(3,4-dichloro-phenoxy)-butyric acid ethyl ester Compound 16c (6.9 g, 90.7%) as a pale pink oil, which was used in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 1.21-1.31 (q, 3H), 2.12-2.25 (m, 2H), 2.45-2.53 (t, 2H), 3.95-4.02 (t, 2H), 4.10-4.20 (q, 2H), 6.71-6.78 (dd, 1H), 6.94-6.96 (d, 1H), 7.28-7.31 (d, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hrs
  2. temperatureThe reaction mixture was refluxed overnight
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organics were dried over MgSO4
  5. filtrationThe drying agent was filtered
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a0b0f47173e24e9286e76f4ae435563e
Source dataset
uspto-grants-2010_09
Patent number
US07799824B2

Reaction notes

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