Potassium Hydroxide → HCID 12251284, compound

HRID 1580263Notes

Reaction equation

HRID 1580263 reaction equation
[C:1]12([CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1)[C:10]1[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:4](=O)[CH2:3][CH2:2]2.O.NN.[OH-].[K+]>C(O)CO>[C:1]12([CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1)[C:10]1[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:4][CH2:3][CH2:2]2

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 12251281HCID 12251281, compound

Product 1

HCID 12251284HCID 12251284, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A solution of 3.63 g. (0.0115 M) of spiro[cyclohexane-1,1'(2'H)-naphthalene]-4,4'(3'H)-dione, 4-(2,2-dimethyltrimethylene ketal(p) (prepared as in Example 14A), 1.54 ml. of hydrazine hydrate and 2.23 g. of potassium hydroxide in 28 ml. of ethylene glycol is heated to reflux. Distillate is collected until the pot temperature rises to 200° C. and refluxing is continued for about 18 hours. The mixture is poured into water and a precipitated material is extracted with ether. The combined extracts are washed with water and brine and then evaporated to dryness. The residue is recrystallized from petroleum ether to give 2.39 g. (69.5% yield) of 3',4'-dihydrospiro[cyclohexane-1,1'(2'H)-naphthalene]-4-one, 2,2-dimethyltrimethylene ketal(q) having a melting point of 109° to 111° C.

Workup

  1. distillationDistillate is collected until the pot temperature
  2. customrises to 200° C.
  3. temperaturerefluxing
  4. additionThe mixture is poured into water
  5. extractiona precipitated material is extracted with ether
  6. washThe combined extracts are washed with water and brine
  7. customevaporated to dryness
  8. customThe residue is recrystallized from petroleum ether
  9. customto give 2.39 g

Sources & evidence

ORD record
ord-eae3e27074fd4053ba02c01390865c52
Source dataset
uspto-grants-1976_01
Patent number
US03932425

Reaction notes

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