1,2-Dichloroethane → (4-Chloro-phenyl)-acetic acid pent-2-enyl ester

HRID 733314Notes

Reaction equation

HRID 733314 reaction equation
[CH2:1]([OH:6])/[CH:2]=[CH:3]/[CH2:4][CH3:5].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15](O)=[O:16])=[CH:10][CH:9]=1.C(Cl)CCl>ClCCl.CN(C1C=CN=CC=1)C>[CH2:1]([O:6][C:15](=[O:16])[CH2:14][C:11]1[CH:12]=[CH:13][C:8]([Cl:7])=[CH:9][CH:10]=1)[CH:2]=[CH:3][CH2:4][CH3:5]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 15880(4-Chlorophenyl)acetic acidHCID 53649202-Penten-1-ol

Product 1

HCID 68576441(4-Chloro-phenyl)-acetic acid pent-2-enyl esterYield 116.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Trans-2-penten-1-ol (49.6 ml; 487.6 mmol) and (4-chloro-phenyl)-acetic acid (83.2 g; 487.6 mmol) were dissolved in 1200 ml of dichloromethane. After addition of EDC (140.2 g, 731 mmol) and DMAP (11.9 g, 97.5 mmol), the reaction mixture was stirred for 18 hours at room temperature. After evaporation under reduced pressure, the residue was dissolved with diethyl ether, washed with water, brine and dried over anhydrous sodium sulfate. Evaporation gave 136 g of an yellow oil, which was further purified by flash-chromatography (silica gel; hexane/ethyl acetate 9:1). Yield: 68 g (59%).

Workup

  1. customAfter evaporation under reduced pressure
  2. dissolutionthe residue was dissolved with diethyl ether
  3. washwashed with water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customEvaporation

Sources & evidence

ORD record
ord-9256b286bea844feaed9660f548a8edf
Source dataset
uspto-grants-2009_09
Patent number
US07589091B2

Reaction notes

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