Formaldehyde → Ethyl 1,3-dihydro-1-oxoisobenzofuran-5-carboxylate

HRID 2247081Notes

Reaction equation

HRID 2247081 reaction equation
OS(O)(=O)=O.O=S(=O)=O.[C:10]([O:22][CH3:23])(=[O:21])[C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1.[CH2:24]=O>C(O)C>[CH2:23]([O:22][C:10]([C:11]1[CH:20]=[C:19]2[C:14](=[CH:13][CH:12]=1)[C:15](=[O:16])[O:17][CH2:18]2)=[O:21])[CH3:24]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8441Dimethyl terephthalateHCID 24681Fuming sulfuric acid

Product 1

HCID 90088Ethyl 1,3-dihydro-1-oxoisobenzofuran-5-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
125 °C

Procedure

Oleum (20-25% SO3, 800 g), dimethyl terephthalate (234 g) and paraformaldehyde (48 g) are heated with stirring for 5 hours at 125° C. The reaction mixture is cooled to 70° C. and poured into ethanol (1,6 L) having room temperature. This mixture is heated to reflux for 1½ hour before ice (800 g) is added. The suspension is stirred overnight, filtered off and washed with ethanol (150 ml). The crude product is suspended in water (800 ml) and pH is adjusted to 4 with NaOH (27%). The precipitate is filtered off and washed with water and dried.

Workup

  1. temperatureThe reaction mixture is cooled to 70° C.
  2. customhaving room temperature
  3. temperatureThis mixture is heated
  4. additionis added
  5. stirringThe suspension is stirred overnight
  6. filtrationfiltered off
  7. washwashed with ethanol (150 ml)
  8. filtrationThe precipitate is filtered off
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-9c4c207576ee418f9137739bb827edc6
Source dataset
uspto-grants-2010_03
Patent number
US07687645B2

Reaction notes

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