HCID 12398824, compound → HCID 21409387, compound

HRID 259510Notes

Reaction equation

HRID 259510 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[CH:20]=[CH:19][C:8]2[C:9](=[O:18])[C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=3[CH:12]=[CH:13][C:7]=2[CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC.O1CCCC1>[O:18]=[C:9]1[C:8]2[CH:19]=[CH:20][C:5]([CH2:4][CH2:3][OH:2])=[CH:6][C:7]=2[CH:13]=[CH:12][C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]1=2

Participants

4

Reactant 2

HCID 12398824HCID 12398824, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21409387HCID 21409387, compound

Reagents, catalysts & solvents 1

HCID 21868444Ether tetrahydrofuranSolvent

Procedure

0.45 G. of methyl(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)acetate is dissolved in 10 ml. of ether/tetrahydrofuran (1:1) and excess lithium aluminum hydride is added. After 3 hours, excess hydride is destroyed by addition of water and the mixture is extracted with ether. The extract is dried and to it is added 2.0 g. of manganese dioxide. The mixture is left for 4 days and then filtered through celite and evaporated. The residue is recrystallized from hexane to afford 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)ethan-1-ol (m.p. 73°-75° C.).

Workup

  1. customexcess hydride is destroyed by addition of water
  2. extractionthe mixture is extracted with ether
  3. customThe extract is dried and to it
  4. additionis added 2.0 g
  5. waitThe mixture is left for 4 days
  6. filtrationfiltered through celite
  7. customevaporated
  8. customThe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-d434f23026fc429085c5c2b2821bc149
Source dataset
uspto-grants-1977_07
Patent number
US04038299

Reaction notes

Loading…