2,3-Dichlorophenol → 3-(2,3-Dichoro-phenoxy)-but-2-enoic acid ethyl ester

HRID 19201

Reaction equation

CC(C)([O-])C.[K+].[Cl:7][C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[OH:15].[CH2:16]([O:18][C:19](=[O:24])[CH:20]=[C:21](Cl)[CH3:22])[CH3:17]>O1CCCC1>[CH2:16]([O:18][C:19](=[O:24])[CH:20]=[C:21]([O:15][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([Cl:14])[C:8]=1[Cl:7])[CH3:22])[CH3:17]

Participants

Conditions

Temperature: 23 °C

Procedure

Potassium t-butoxide (11.2 g, 0.100 mol) was added to a stirred solution of 2,3-dichlorophenol (8.2 g, 0.05 mol) in tetrahydrofuran (40 mL) at 23° C. under nitrogen and the reaction mixture was heated to reflux for 0.75 h. The reaction mixture was cooled to 23° C. and a solution of 3-chloro-but-2-enoic acid ethyl ester (6.5 g, 0.044 mol) in tetrahydrofuran (40 mL) was added to the reaction mixture. The reaction mixture was refluxed for an additional 3 h. After this time, the mixture was concentrated in vacuo and the residue was diluted with water and extracted with diethyl ether. The organic layer was then washed with 5% sodium hydroxide solution followed by a saturated sodium chloride solution. The combined organic layers were separated, dried over sodium sulfate and concentrated in vacuo to afford 3-(2,3-dichoro-phenoxy)-but-2-enoic acid ethyl ester (9.20 g, 76%) as a yellow oil.

Workup

temperaturethe reaction mixture was heated
temperatureto reflux for 0.75 h
temperatureThe reaction mixture was refluxed for an additional 3 h
concentrationAfter this time, the mixture was concentrated in vacuo
additionthe residue was diluted with water
extractionextracted with diethyl ether
washThe organic layer was then washed with 5% sodium hydroxide solution
customThe combined organic layers were separated
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-cd203e1fa6ee4bb7a2d6bf3bdf2a757a
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Linked notes

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