Acetic Acid → HCID 14098154, compound

HRID 569274Notes

Reaction equation

HRID 569274 reaction equation
Cl[CH2:2][CH2:3][C:4]1[C:5](=[O:17])[C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH3:14])=[C:8]([Cl:15])[C:7]=2[Cl:16].O.[C:19]([OH:22])(=[O:21])[CH3:20]>C([O-])(=O)C.[Ag+]>[C:19]([O:22][CH2:2][CH2:3][C:4]1[C:5](=[O:17])[C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH3:14])=[C:8]([Cl:15])[C:7]=2[Cl:16])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 14098153HCID 14098153, compound

Product 1

HCID 14098154HCID 14098154, compound

Reagents, catalysts & solvents 1

HCID 11246Silver acetateCatalyst

Conditions

Temperature
105 °C

Procedure

2-(2-Chloroethyl)-6,7-dichloro-5-methoxy-1H-inden-1-one (18.4 g, 0.0619 mole) and silver acetate (22.7 g, 0.1362 mole) were suspended in acetic acid (225 ml) and water (2 ml) and the mixture stirred and heated at 105° C. for 9 hours and at ambient temperature for 16 hours. The mixture was filtered and the residue on the funnel washed with ethyl acetate. The combined filtrate were evaporated in vacuo and the residue suspended in water. The mixture was extracted first with 10% tetrahydofuran in ether, then with methylene chloride and finally with ethyl acetate. The combined organic extracts were washed with water, then with brine. After drying over MgSO4 the combined organic extracts were evaporated in vacuo. The residue was treated with warm ethyl acetate (10 ml) and tetrahydrofuran (10 ml) and then cooled. The solid that formed was removed by filtration with an equal mixture of ethyl acetate and hexane and dried to give 2-(acetoxyethyl)-6,7-dichloro-5-methoxy-1H-inden-1-one, 8.1 g, m.p. 134°-136° C.

Workup

  1. filtrationThe mixture was filtered
  2. washthe residue on the funnel washed with ethyl acetate
  3. customThe combined filtrate were evaporated in vacuo
  4. extractionThe mixture was extracted first with 10% tetrahydofuran in ether
  5. washThe combined organic extracts were washed with water
  6. dry with materialAfter drying over MgSO4 the combined organic extracts
  7. customwere evaporated in vacuo
  8. additionThe residue was treated with warm ethyl acetate (10 ml) and tetrahydrofuran (10 ml)
  9. temperaturecooled
  10. customThe solid that formed
  11. customwas removed by filtration with an equal mixture of ethyl acetate and hexane
  12. customdried

Sources & evidence

ORD record
ord-03112f99491d4188bbdc4b143b3ead3f
Source dataset
uspto-grants-1988_03
Patent number
US04731470

Reaction notes

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