Methanol → HCID 12533760, compound

HRID 1065513Notes

Reaction equation

HRID 1065513 reaction equation
[CH3:1][CH:2]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][C:6](=[O:14])[CH2:5][C:4]2[CH:15]=[CH:16][CH:17]=[CH:18][C:3]1=2.CO.[BH4-].[Na+]>[OH-].[Na+].O>[CH3:1][CH:2]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH:6]([OH:14])[CH2:5][C:4]2[CH:15]=[CH:16][CH:17]=[CH:18][C:3]1=2

Participants

6

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 12533759HCID 12533759, compound

Product 1

HCID 12533760HCID 12533760, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 962WaterSolvent

Procedure

12-Methyl-5,6,7,12-tetrahydrodibenzo[a,d]cycloocten-6-one (3.6 g., 15.3 mmole) in 25 ml. of methanol was treated with several drops of 1 M sodium hydroxide followed by 0.58 g. (15.3 mmole) of sodium borohydride in 5 ml. of water. The mixture was heated at reflux for 20 minutes, cooled, and concentrated in vacuo. The residue was slurried in water and extracted three times with chloroform. The chloroform fractions were washed with water, dried over sodium sulfate, filtered, and evaporated in vacuo to give 3.7 g. of white solid, m.p. 142°-145° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 20 minutes
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. extractionextracted three times with chloroform
  6. washThe chloroform fractions were washed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customto give 3.7 g

Sources & evidence

ORD record
ord-1a1f360684694648a23c1992957095da
Source dataset
uspto-grants-1982_05
Patent number
US04329465

Reaction notes

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