Dimethyl 5-(hydroxymethyl)isophthalate → Dimethyl 5-formylisophthalate

HRID 587935Notes

Reaction equation

HRID 587935 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:13]([O:15][CH3:16])=[O:14])[CH:6]=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9]>C(Cl)Cl.O=[Mn]=O>[CH:2]([C:3]1[CH:12]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[CH:6]=[C:5]([CH:4]=1)[C:13]([O:15][CH3:16])=[O:14])=[O:1]

Participants

4

Reactant 1

HCID 13907324Dimethyl 5-(hydroxymethyl)isophthalate

Product 1

HCID 15183982Dimethyl 5-formylisophthalate

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.15 g (14.1 mmol) of dimethyl 5-(hydroxymethyl)isophthalate (prepared as described in Dimick et al., J. Am. Chem. Soc. (1999) 121, No. 44, 10286-10296) in 60 mL of DCM was added 7.34 g (84.4 mmol) of MnO2. The mixture was stirred at reflux for about 16 h and an additional 3.5 g of MnO2 was added. Refluxing was continued for another 6 h and the mixture was cooled, filtered through celite and evaporated to give dimethyl 5-formylisophthalate as a white solid which was used subsequently without purification.

Workup

  1. temperatureat reflux for about 16 h
  2. temperatureRefluxing
  3. temperaturethe mixture was cooled
  4. filtrationfiltered through celite
  5. customevaporated

Sources & evidence

ORD record
ord-55c2bff881f5483c9e30f898767e27a1
Source dataset
uspto-grants-2016_01
Patent number
US09227918B2

Reaction notes

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