1,4-Dioxaspiro[4.5]decan-8-ylmethanol → 9-Benzoyl-3-hydroxymethyl-1,2,3,4-tetrahydrocarbazole

HRID 1605104Notes

Reaction equation

HRID 1605104 reaction equation
Cl.[C:2]([N:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)N)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1O[C:21]2([CH2:26][CH2:25][CH:24]([CH2:27][OH:28])[CH2:23][CH2:22]2)OC1>C(O)C>[C:2]([N:10]1[C:21]2[CH2:26][CH2:25][CH:24]([CH2:27][OH:28])[CH2:23][C:22]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 100808381,4-Dioxaspiro[4.5]decan-8-ylmethanolHCID 121972221-Benzoyl-1-phenylhydrazine hydrochloride

Product 1

HCID 214316619-Benzoyl-3-hydroxymethyl-1,2,3,4-tetrahydrocarbazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1Benzoyl-1phenylhydrazine hydrochloride (23.8 g.) and 18 g. of 4-hydroxymethylcyclohexanone ethylene ketal in 450 ml. of absolute ethyl alcohol was heated under reflux for four hours. The chilled mixture was filtered, the filtrate was evaporated to dryness under reduced pressure and the resulting residue was dissolved in ether. The ether solution was washed with water, dilute hydrochloric acid, water, dilute sodium bicarbonate, and water, dried and evaporated to dryness to give, after recrystallization from ethyl acetate-hexane, 9.6 g. of 9-benzoyl-3-hydroxymethyl-1,2,3,4-tetrahydrocarbazole; m.p. 105°-107°C.

Workup

  1. temperatureunder reflux for four hours
  2. filtrationThe chilled mixture was filtered
  3. customthe filtrate was evaporated to dryness under reduced pressure
  4. dissolutionthe resulting residue was dissolved in ether
  5. washThe ether solution was washed with water, dilute hydrochloric acid, water, dilute sodium bicarbonate, and water
  6. customdried
  7. customevaporated to dryness
  8. customto give
  9. customafter recrystallization from ethyl acetate-hexane, 9.6 g

Sources & evidence

ORD record
ord-1ea342d13e334220b353f4b251582fcf
Source dataset
uspto-grants-1976_04
Patent number
US03948939

Reaction notes

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