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

HRID 1985990Notes

Reaction equation

HRID 1985990 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 was heated under reflux for 16 hours. The reaction was then cooled to room temperature and the solvent was removed in vacuo. The residue was partitioned between saturated aqueous sodium hydrogen carbonate solution (300 mL) and ethyl acetate (500 mL). The organic phase was separated and washed with water (200 mL) and brine (300 mL), dried over sodium sulfate and the concentrated in vacuo to afford the title compound as a pale yellow oil in quantitative yield, 63.5 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. temperaturethe resulting solution was heated
  2. temperatureunder reflux for 16 hours
  3. customthe solvent was removed in vacuo
  4. customThe residue was partitioned between saturated aqueous sodium hydrogen carbonate solution (300 mL) and ethyl acetate (500 mL)
  5. customThe organic phase was separated
  6. washwashed with water (200 mL) and brine (300 mL)
  7. dry with materialdried over sodium sulfate
  8. concentrationthe concentrated in vacuo

Sources & evidence

ORD record
ord-1e0a6f74e5894c97ad7fd5d66cbaa887
Source dataset
uspto-grants-2009_06
Patent number
US07547731B2

Reaction notes

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