Ethanol → Diethyl 2,2'-(1,3-phenylene)diacetate

HRID 898495Notes

Reaction equation

HRID 898495 reaction equation
[C:1]1([CH2:11][C:12]([OH:14])=[O:13])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]([OH:10])=[O:9])[CH:2]=1.[C:15](Cl)(=O)[CH3:16].[CH2:19](O)[CH3:20]>>[C:1]1([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]([O:10][CH2:19][CH3:20])=[O:9])[CH:2]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 6367Acetyl chlorideHCID 29788m-Phenylenediacetic acid

Product 1

HCID 19863769Diethyl 2,2'-(1,3-phenylene)diacetate

Procedure

2,2′-(1,3-phenylene)diacetic acid (10.0 g, 51 mmol) was dissolved in ethanol (100 ml) and the solution treated dropwise with catalytic acetyl chloride (2.5 ml). The reaction mixture was stirred at reflux for 18 hours before being allowed to cool and concentrated in vacuo. The residue was taken up in ethyl acetate (100 ml) and extracted with sodium bicarbonate solution (3×50 ml) and brine (3×50 ml). The organic phase was then dried (magnesium sulphate) and concentrated in vacuo. The residue was triturated with pentane to yield the title product, 11.8 g.

Workup

  1. temperatureat reflux for 18 hours
  2. temperatureto cool
  3. concentrationconcentrated in vacuo
  4. extractionextracted with sodium bicarbonate solution (3×50 ml) and brine (3×50 ml)
  5. dry with materialThe organic phase was then dried (magnesium sulphate)
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with pentane

Sources & evidence

ORD record
ord-9f960cc148554feb9aa4b21789112015
Source dataset
uspto-grants-2008_04
Patent number
US07351742B2

Reaction notes

Loading…