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

HRID 907075Notes

Reaction equation

HRID 907075 reaction equation
[C:1](Cl)(=O)[CH3:2].[C:5]1([CH2:15][C:16]([OH:18])=[O:17])[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][C:12]([OH:14])=[O:13])[CH:6]=1.[CH2:19](O)[CH3:20]>>[C:5]1([CH2:15][C:16]([O:18][CH2:1][CH3:2])=[O:17])[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][C:12]([O:14][CH2:19][CH3:20])=[O:13])[CH:6]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 6367Acetyl chlorideHCID 29788m-Phenylenediacetic acid

Product 1

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

Procedure

Acetyl chloride (12.5 ml, 175 mmol) was added to a suspension of 2,2′-(1,3-phenylene)diacetic acid (50.0 g, 260 mmol) in ethanol (500 ml) and the resulting solution heated to reflux for 16 hours. The reaction was cooled to room temperature and the solvent removed in vacuo. The residue was partitioned between saturated aqueous sodium hydrogencarbonate (300 ml) and ethyl acetate (500 ml). The organic phase was washed with water (200 ml), sat. aq. sodium chloride (300 ml), dried (sodium sulfate) and the solvent removed in vacuo to give the title compound as a pale yellow oil (63.5 g).

Workup

  1. temperaturethe resulting solution heated
  2. temperatureto reflux for 16 hours
  3. customthe solvent removed in vacuo
  4. customThe residue was partitioned between saturated aqueous sodium hydrogencarbonate (300 ml) and ethyl acetate (500 ml)
  5. washThe organic phase was washed with water (200 ml), sat. aq. sodium chloride (300 ml)
  6. dry with materialdried (sodium sulfate)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-2cca59e19077471e9dd4ad2db733c11f
Source dataset
uspto-grants-2011_09
Patent number
US08013019B2

Reaction notes

Loading…