Ethyl 2-chloropropionate → Propanoic acid, 2-[4-[(3,5-dichloro-2-pyridinyl)oxy]phenoxy]-, ethyl ester

HRID 1108943Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:9]([O:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[N:10][CH:11]=[C:12]([Cl:14])[CH:13]=1.Cl[CH:24]([CH3:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26].C1(C)C=CC=CC=1.CCCCCCC>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.O.C1OCCOCCOCCOCCOCCOC1>[Cl:7][C:8]1[C:9]([O:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH:24]([CH3:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:18][CH:17]=2)=[N:10][CH:11]=[C:12]([Cl:14])[CH:13]=1

Participants

Conditions

Temperature: 85 °C

Procedure

Potassium carbonate (867 g, 6.29 mol) is added to a mixture of p-[(3,5-dichloro-2-pyridyl)oxy]phenol (1,609 g, 6.29 mol), 18-crown-6 (50 g, 0.19 mol) and tetrabutylammonium hydrogen sulfate (50 g, 0.15 mol) in dimethylformamide (20 L). Ethyl 2-chloropropionate (1,380 g, 10.10 mol) is then added and the reaction mixture is stirred for 2 days at 85° C., diluted with water and extracted with methylene chloride. The combined organic extracts are washed sequentially with water, 2% sodium hydroxide solution and water and concentrated in vacuo to give a residue. The residue is dissolved into a 1:1 toluene/heptane solution, washed with 2% sodium hydroxide solution and concentrated in vacuo to obtain the title product as a dark red-brown liquid (1,445 g) which is identified by 1HNMR spectral analysis.

Workup

extractionextracted with methylene chloride
washThe combined organic extracts are washed sequentially with water, 2% sodium hydroxide solution and water
concentrationconcentrated in vacuo
customto give a residue
washwashed with 2% sodium hydroxide solution
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-23f5e19c43364d0b9c4ea09a4368ffd9
Source dataset: uspto-grants-1994_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05318946

Reaction notes

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