Hydrochloric Acid → 5'-Ethoxyspiro(cyclohexane-1,2'-indan)-1',4-dione 4-ethylene ketal

HRID 1580274Notes

Reaction equation

HRID 1580274 reaction equation
C1C2C(=CC=CC=2)CCC21CC[C:13](=[O:16])[CH2:12]C2.[CH2:17]([O:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[C:25](=[O:29])[C:24]1([CH2:34][CH2:33][C:32](=[O:35])[CH2:31][CH2:30]1)[CH2:23]2)[CH3:18].Cl>CC(C)=O>[CH2:13]1[O:16][C:25]2([C:26]3[C:22](=[CH:21][C:20]([O:19][CH2:17][CH3:18])=[CH:28][CH:27]=3)[CH2:23][C:24]32[CH2:34][CH2:33][C:32](=[O:35])[CH2:31][CH2:30]3)[O:29][CH2:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12251269HCID 12251269, compoundHCID 541367305'-Ethoxyspiro(cyclohexane-1,2'-indan)1', 4-dione

Product 1

HCID 867329365'-Ethoxyspiro(cyclohexane-1,2'-indan)-1',4-dione 4-ethylene ketal

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.86 g. (0.0072 mole) of 3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-one, ethylene ketal (8) (prepared in Example 7C) and 2 ml. of 2.5 N hydrochloric acid in 40 ml. of acetone is heated at reflux for about 17 hours. Most of the solvent is removed under vacuum and the residue dissolved in water and ether. The organic layer is washed with water and brine and then evaporated to dryness to give 3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-one (9).

Workup

  1. additionA mixture of 1.86 g
  2. temperatureat reflux for about 17 hours
  3. customMost of the solvent is removed under vacuum
  4. dissolutionthe residue dissolved in water
  5. washThe organic layer is washed with water and brine
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-6c703c7e9bbb4b5c93c61ea6e078cf2c
Source dataset
uspto-grants-1976_01
Patent number
US03932425

Reaction notes

Loading…