Methanol → HCID 12533760, compound

HRID 1758724Notes

Reaction equation

HRID 1758724 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-3a8b2fc5d46844deb79e21c8dc4f3d8d
Source dataset
uspto-grants-1983_02
Patent number
US04374838

Reaction notes

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