Acetic Acid → HCID 12806958, compound

HRID 2058585Notes

Reaction equation

HRID 2058585 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]([O:12][CH3:13])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH2:6]2.C(O)(=[O:16])C>O.[O-2].[O-2].[O-2].[Cr+6]>[Cl:11][C:10]1[C:2]([Cl:1])=[C:3]2[C:7]([CH2:6][CH2:5][C:4]2=[O:16])=[CH:8][C:9]=1[O:12][CH3:13]

Participants

5

Reactant 2

HCID 176Acetic Acid2×HCID 12806962HCID 12806962, compound

Product 1

HCID 12806958HCID 12806958, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent2×

Procedure

4,5-Dichloro-6-methoxy-2,3-dihydro-1H-indene (21 gm., 0.097 mole) is dissolved in acetic acid (280 ml.) and chromium trioxide (14 gm., 0.14 mole) in a mixture of water (15 ml.) and acetic acid (40 ml.) is added dropwise with stirring over a period of one hour. The mixture is poured, with stirring into cold water (1200 ml.) and the solid that separates is removed by filtration, washed with water and dried. The product, which consists of a mixture of the desired material and the isomer described in Step D, is subjected to column chromatographic separation using 225 gm. of silica gel and chloroform is used for elution. Evaporation of the solvent gives 6,7-dichloro-5-methoxy-2,3-dihydro-1H-inden-1-one, 5.2 gm., m.p. 154°-156° C.

Workup

  1. additionis added dropwise
  2. additionThe mixture is poured
  3. customthe solid that separates is removed by filtration
  4. washwashed with water
  5. customdried
  6. additionThe product, which consists of a mixture of the desired material
  7. customis subjected to column chromatographic separation
  8. washof silica gel and chloroform is used for elution
  9. customEvaporation of the solvent

Sources & evidence

ORD record
ord-898dd22670ba4acc927a62644048af5c
Source dataset
uspto-grants-1982_03
Patent number
US04317922

Reaction notes

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