Acetic Acid → HCID 14099848, compound

HRID 569299Notes

Reaction equation

HRID 569299 reaction equation
Cl[CH2:2][CH2:3][CH:4]1[CH2:12][C:11]2[C:6](=[C:7]([Cl:16])[C:8]([Cl:15])=[C:9]([O:13][CH3:14])[CH:10]=2)[C:5]1=[O:17].[C:18]([OH:21])(=[O:20])[CH3:19].O>CCOCC.C([O-])(=O)C.[Ag+]>[C:18]([O:21][CH2:2][CH2:3][CH:4]1[CH2:12][C:11]2[C:6](=[C:7]([Cl:16])[C:8]([Cl:15])=[C:9]([O:13][CH3:14])[CH:10]=2)[C:5]1=[O:17])(=[O:20])[CH3:19]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 14099847HCID 14099847, compound

Product 1

HCID 14099848HCID 14099848, compound

Reagents, catalysts & solvents 2

HCID 11246Silver acetateCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
105 °C

Procedure

2-(2-Chloroethyl)-6,7-dichloro-2,3-dihydro-5-methoxy-1H-inden-1-one (18.14 gm, 0.0619 mole), silver acetate (22.74 gm, 0.136 mole), acetic acid (225 ml) and water (2 ml) was stirred and heated at 105° C. internal temperature for 9 hours, then at ambient temperature for 16 hours. The mixture was diluted with ether, filtered and the solid washed with ethyl acetate. The combined filtrate and washing was evaporated in vacuo and the reside suspended in water then extracted first with a mixture of ether and tetrahydrofuran, then with methylene chloride and finally with ethyl acetate. The combined organic extracts were washed with water, then with brine and finally dried over MgSO4. The solvents were removed by evaporation in vacuo to give 12.9 g of residual solid. The solid was recrystallized from a mixture of ethyl acetate and tetrahydrofuran to give 8.1 g of product, m.p. 134°-136° C.

Workup

  1. filtrationfiltered
  2. washthe solid washed with ethyl acetate
  3. washThe combined filtrate and washing
  4. customwas evaporated in vacuo
  5. extractionthen extracted first with a mixture of ether and tetrahydrofuran
  6. washThe combined organic extracts were washed with water
  7. dry with materialwith brine and finally dried over MgSO4
  8. customThe solvents were removed by evaporation in vacuo

Sources & evidence

ORD record
ord-398befd6d9694cc7be82514aab2da1ef
Source dataset
uspto-grants-1988_03
Patent number
US04731471

Reaction notes

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