HCID 68670470, compound → HCID 59570145, compound

HRID 2071126Notes

Reaction equation

HRID 2071126 reaction equation
[OH:1][CH:2]([C:4]1[CH:5]=[C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:7]=[C:8]([CH:14]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:3]>O=[Mn]=O>[C:2]([C:4]1[CH:14]=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:7]=[C:6]([CH:5]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:1])[CH3:3]

Participants

3

Reactant 1

HCID 68670470HCID 68670470, compound

Product 1

HCID 59570145HCID 59570145, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 14801Manganese dioxideCatalyst2×

Procedure

A stirred solution of diethyl 5-(1-hydroxyethyl)isophthalate (587 mg, 2.2 mmol) and MnO2 (960 mg, 11 mmol) was heated to reflux. After 5 h, the reaction was cooled to room temperature and additional MnO2 (0.6 g) was added and heated to reflux for another 16 h. The reaction mixture was cooled to room temperature and filtered through Celite. The filtrate was concentrated to provide diethyl 5-acetylisophthalate (521 mg, 90%) as a white solid. 1H NMR (CDCl3): d 8.62 (s, 1H), 8.56 (s, 2H), 4.32 (q, J=7.2 Hz, 2H), 2.58 (s, 3H), 1.32 (t, J=7.2 Hz, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux for another 16 h
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfiltered through Celite
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8d014c84bba745e09e1c3d3a318aa491
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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