Acetic Acid → HCID 12806958, compound

HRID 1157041Notes

Reaction equation

HRID 1157041 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>[Cr].O>[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 962WaterSolvent2×HCID 23976ChromiumSolvent

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-e23566296dc64fbbbaf84350e4866b59
Source dataset
uspto-grants-1982_06
Patent number
US04337354

Reaction notes

Loading…