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

HRID 494415Notes

Reaction equation

HRID 494415 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 under reduced pressure. The residue was taken up in ethyl acetate (100 mL) and washed with sodium bicarbonate solution (3×50 mL) and brine (3×50 mL). The organic phase was dried over magnesium sulphate and concentrated under reduced pressure. 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 under reduced pressure
  4. washwashed with sodium bicarbonate solution (3×50 mL) and brine (3×50 mL)
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with pentane

Sources & evidence

ORD record
ord-9bd19ea7716141d087555c03aeb06612
Source dataset
uspto-grants-2009_05
Patent number
US07538141B2

Reaction notes

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