1,4-Dioxane → HCID 22750700, compound

HRID 1606132Notes

Reaction equation

HRID 1606132 reaction equation
[CH3:1][C:2]1[C:12]2[CH:11]=[CH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.O1CCOCC1.[BH4-].[Na+]>O>[OH:17][CH:7]1[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[C:12]=2[CH:11]=[CH:10][C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][C:8]1=2

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 4311764Sodium borohydrideHCID 200675891-Methyl-5H-dibenzo[a,d]cyclohepten-5-one

Product 1

HCID 22750700HCID 22750700, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

26 g. of 1-Methyl-5H-dibenzo[a,d]cyclohepten-5-one are dissolved in 200 ml. of dioxane, a solution of 9 g. of sodium borohydride in 35 ml. of water is added thereto and the mixture is stirred at room temperature for 4 hours. The mixture is subsequently evaporated under reduced pressure. The residue is shaken with ether and water. The ethereal phase is washed with water, dried over sodium sulfate, filtered and evaporated. The 5-hydroxy-1-methyl-5H-dibenzo[a,d]cycloheptene obtained is recrystallized from petroleum ether and melts at 114°-116°C.

Workup

  1. customThe mixture is subsequently evaporated under reduced pressure
  2. stirringThe residue is shaken with ether and water
  3. washThe ethereal phase is washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-375afe31570e4ef2bf7c412364e4c03d
Source dataset
uspto-grants-1976_04
Patent number
US03952017

Reaction notes

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