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

HRID 1295396Notes

Reaction equation

HRID 1295396 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]>>[CH2:19]([O:9][C:8](=[O:10])[CH2:7][C:3]1[CH:4]=[CH:5][CH:6]=[C:1]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:2]=1)[CH3:20]

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 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 dried (MgSO4), concentrated in vacuo and the residue triturated with pentane to yield the product (11.8 g). 1HNMR (CDCl3, 400 MHz) δ: 1.31 (6H, t), 3.65 (4H, s), 4.20 (4H, q), 7.24–7.36 (4H, m); LRMS ESI m/z 251 [M+H]+

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 dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customthe residue triturated with pentane

Sources & evidence

ORD record
ord-5d4aa405514840a68854f8c3a8c8e6a1
Source dataset
uspto-grants-2007_07
Patent number
US07241810B2

Reaction notes

Loading…