Water → HCID 21419381, compound

HRID 441577Notes

Reaction equation

HRID 441577 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([NH:10][CH:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:23][CH3:24])[C:17]=2[O:21][CH3:22])[C:12]1=[O:25])(=[O:9])[CH3:8].O.[OH-].[Na+]>O1CCCC1>[OH:25][CH:12]1[C:13]2[C:18](=[C:17]([O:21][CH3:22])[C:16]([O:23][CH3:24])=[CH:15][CH:14]=2)[CH2:19][CH2:20][CH:11]1[NH:10][C:7](=[O:9])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2×HCID 21419380HCID 21419380, compound

Product 1

HCID 21419381HCID 21419381, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.32 part of lithium aluminum hydride in dry tetrahydrofuran, there is added 1.6 parts of 3,4-dihydro-2-acetamido-5,6-dimethoxy-1(2H)-naphthalenone in small portions. After the addition has been completed, the mixture is further stirred for 20 minutes, at the end of which time water is added so as to decompose the lithium aluminum hydride. The mixture is rendered sufficiently alkaline by the addition of a 3N aqueous solution of sodium hydroxide and, then, extracted with chloroform. The chloroform layer is washed with water and dried over anhydrous sodium sulfate. The chloroform is distilled off and the residue is treated with ethanol. The procedure gives crystals of 1-hydroxy-2-acetamido-5,6-dimethoxy-1,2,3,4-tetrahydronaphthalene. Melting point 184°-186° C.

Workup

  1. additionAfter the addition
  2. additionis added so as
  3. extractionextracted with chloroform
  4. washThe chloroform layer is washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe chloroform is distilled off
  7. additionthe residue is treated with ethanol

Sources & evidence

ORD record
ord-b800df1e338a4b4eb0ad8d8ba7ffdc74
Source dataset
uspto-grants-1977_08
Patent number
US04041079

Reaction notes

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