Water → Propanoic acid, 2-chloro-, oxydi-2,1-ethanediyl ester

HRID 1398262Notes

Reaction equation

HRID 1398262 reaction equation
[CH2:1]([OH:7])[CH2:2][O:3][CH2:4][CH2:5][OH:6].[Cl:8][CH:9]([CH3:13])[C:10]([OH:12])=O.[OH2:14]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:8][CH:9]([CH3:13])[C:10]([O:7][CH2:1][CH2:2][O:3][CH2:4][CH2:5][O:6][C:10](=[O:12])[CH:9]([Cl:8])[CH3:13])=[O:14]

Participants

6

Reactant 3

HCID 962WaterHCID 8117Diethylene GlycolHCID 117342-Chloropropionic acid

Product 1

HCID 346305Propanoic acid, 2-chloro-, oxydi-2,1-ethanediyl ester

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

In a 20 L glass reactor equipped with a Dean-Stark apparatus was added a solution of diethylene glycol (1500 g), 2-chloropropionic acid (3200 g) and para-toluene sulphonic acid (50 g) in toluene (5 L). The reaction mixture was refluxed for 5 hours with azeotropic removal of water, and then cooled to room temperature. The toluene layer was washed with 5% sodium bicarbonate solution (4500 ml) and water (4 L). The toluene layer was dried over anhydrous anhydrous sodium sulphate, and distilled to obtain 2-chloropropionic acid 2-[2-(2-chloropropionyloxy)-ethoxy]-ethyl ester (3.3 Kg) as light yellow oil. The product was characterized by 1H NMR (CDCl3) δ 1.65 (d, 3H, CH3), 3.75 (t, 2H, CH2), 4.40 (t, 2H, CH2), 4.48 (q, 1H, CH)

Workup

  1. customIn a 20 L glass reactor equipped with a Dean-Stark apparatus
  2. washThe toluene layer was washed with 5% sodium bicarbonate solution (4500 ml) and water (4 L)
  3. dry with materialThe toluene layer was dried over anhydrous anhydrous sodium sulphate
  4. distillationdistilled

Sources & evidence

ORD record
ord-3d37eef0489d4fb79ad16bed1dbef63c
Source dataset
uspto-grants-2014_12
Patent number
US08901347B1

Reaction notes

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