Ethanol → 1H-Indene-1,3(2H)-dione, 2-(3-methoxyphenyl)-

HRID 326436

Reaction equation

HRID 326436 reaction equation
[Na].O1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][C:3]1=[O:11].CO[C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=[O:18].O.[CH2:23]([OH:25])C>C(O)(=O)C>[CH3:23][O:25][C:9]1[CH:10]=[C:5]([CH:4]2[C:3](=[O:11])[C:19]3[C:16](=[CH:15][CH:14]=[CH:21][CH:20]=3)[C:17]2=[O:18])[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 5

HCID 702EthanolHCID 962WaterHCID 115693-MethoxybenzaldehydeHCID 683822(3H)-BenzofuranoneHCID 5360545Sodium

Product 1

HCID 28178101H-Indene-1,3(2H)-dione, 2-(3-methoxyphenyl)-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
20 °C

Procedure

Sodium (18.9 parts) was dissolved in absolute ethanol (380 parts) with stirring and was cooled to 20° C. and benzofuranone (100 parts) and 3-methoxybenzaldehyde were added. The reaction mixture was stirred under reflux for 15 minutes and cooled to 20° C. over 1 hour. The reaction mixture was poured into water (900 parts) and the ethanol was removed by evaporation under reduced pressure. Hydrochloric acid was added to the solution until acid and the aqueous phase was decanted to leave a red gum. The gum was dissolved in hot acetic acid (300 parts) and the solution was cooled to 20° C. and a solid was precipitated. The solid was isolated by filtration, washed with ethanol (74 OP) and dried to give 2-(3-methoxyphenyl)-1,3-indandione (55.8 parts) m.pt. 142°-144° C.

Workup

  1. stirringThe reaction mixture was stirred
  2. temperatureunder reflux for 15 minutes
  3. temperaturecooled to 20° C. over 1 hour
  4. customthe ethanol was removed by evaporation under reduced pressure
  5. additionHydrochloric acid was added to the solution until acid
  6. customthe aqueous phase was decanted
  7. customto leave a red gum
  8. temperaturethe solution was cooled to 20° C.
  9. customa solid was precipitated
  10. customThe solid was isolated by filtration
  11. washwashed with ethanol (74 OP)
  12. customdried

Sources & evidence

ORD record
ord-5ea19ccd8fb94115bcee3275454afcb0
Source dataset
uspto-grants-1993_12
Patent number
US05268490

Linked notes

Loading…