HCID 20545909, compound → HCID 20545923, compound

HRID 2059312Notes

Reaction equation

HRID 2059312 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])=[CH:15][CH:16]=3)[C:11](=[O:24])[C:10]([CH3:26])([CH3:25])[CH2:9]2)=[CH:4][CH:3]=1.[H-].[Li+].[Al+3].[H-].[H-].[H-]>CCOCC.[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH2:19][CH2:20][N:21]([CH3:22])[CH3:23])=[CH:15][CH:16]=3)[CH:11]([OH:24])[C:10]([CH3:26])([CH3:25])[CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 20545909HCID 20545909, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20545923HCID 20545923, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 4-(4-chlorophenyl)-2,2-dimethyl-7-(2-dimethylaminoethoxy)-1-tetralone (13.6 g) in dry ether (75 ml) was added to a stirred suspension of aluminium lithium hydride (1.3 g) in dry ether (75 ml) over 40 min. The mixture was heated under reflux a further 45 min., cooled, a few drops of dilute sodium hydroxide solution added, and the ether solution decanted off. The remaining pasty mass was extracted with hot ether, and the combined ether solutions were dried (MgSO4). Removal of the solvent gave 4-(4-chlorophenyl)-1-hydroxy-2,2-dimethyl-7-(2-dimethylaminoethoxy)tetralin as a white foam. (13.3 g, 98%). The hydrochloride salt formed white prisms from ethanol-ether, m.p. 235°-7°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux a further 45 min.
  3. temperaturecooled
  4. customthe ether solution decanted off
  5. extractionThe remaining pasty mass was extracted with hot ether
  6. dry with materialthe combined ether solutions were dried (MgSO4)
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-b47ca4662c194180baac20e69774d625
Source dataset
uspto-grants-1982_03
Patent number
US04322370

Reaction notes

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