Hydrochloric Acid → HCID 12251437, compound

HRID 1580269Notes

Reaction equation

HRID 1580269 reaction equation
C1O[C:4]2([CH2:18][CH2:17][C:7]3([CH2:15][C:14]4[C:9](=[CH:10][C:11](C)=[CH:12][CH:13]=4)[CH2:8]3)[CH2:6][CH2:5]2)[O:3]C1.Cl>CC(C)=O>[CH2:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:15][C:7]21[CH2:17][CH2:18][C:4](=[O:3])[CH2:5][CH2:6]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86732934HCID 86732934, compound

Product 1

HCID 12251437HCID 12251437, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4g. (0.016 M) of spiro(cyclohexane-1,2'-indan)-4-one ethylene ketal [10] (prepared in Example 20B) and 8 ml. of 2.5 N hydrochoric acid in 80 ml. of acetone is heated at reflux for about 4 hours. Most of the solvent is removed under vacuum and ether added. The organic layer is separated, washed with water and brine and evaporated to dryness. The residue is chromatographed on a 350 ml. column of silica gel with elution by methylene chloride. Those fractions similar by thin layer chromatography are combined to give spiro(cyclohexane-1,2'-indan)-4-one [11] as an amorphous gum.

Workup

  1. temperatureat reflux for about 4 hours
  2. customMost of the solvent is removed under vacuum and ether
  3. additionadded
  4. customThe organic layer is separated
  5. washwashed with water and brine
  6. customevaporated to dryness
  7. customThe residue is chromatographed on a 350 ml
  8. washcolumn of silica gel with elution by methylene chloride

Sources & evidence

ORD record
ord-f03d3ac73a0145ad96a502016636ce75
Source dataset
uspto-grants-1976_01
Patent number
US03932425

Reaction notes

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