Diethyl Ether → 6-Methoxy-1-tetralone oxime

HRID 1164705Notes

Reaction equation

HRID 1164705 reaction equation
[K].CCOCC.[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=O)[CH2:14][CH2:13][CH2:12]2.[N:20](OCCCC)=[O:21]>C(O)(C)(C)C>[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[N:20][OH:21])[CH2:14][CH2:13][CH2:12]2

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10996Butyl nitriteHCID 141126-Methoxy-alpha-tetraloneHCID 5462222Potassium

Product 1

HCID 52161626-Methoxy-1-tetralone oximeYield 12%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

In 60 ml of refluxing t-butanol was dissolved 3.84 g (0.0985 mole) of potassium. Ether (150 ml) was added followed by 15.87 g (0.09 mole) of 6-methoxy-1-tetralone. Butyl nitrite (11.1 g, 0.0932 mole) was added dropwise with stirring over a period of 30 minutes. The insoluble salts were filtered and washed with ether. They were slurried with 180 ml of water and then 15 ml of Concentrated HCl was added. The initially formed oil solidified. The solid was filtered and washed with water. Recrystallization of the still damp product from 250 ml of ethanol gave 8.86 g. Concentration of the filtrate to 1/3 volume gave 2.06 g additional material. Total yield 10.92 g (59%). A second recrystallization gave an analytical sample, mp 168°-171° dec.

Workup

  1. filtrationThe insoluble salts were filtered
  2. washwashed with ether
  3. addition15 ml of Concentrated HCl was added
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. customRecrystallization of the still damp product from 250 ml of ethanol
  7. customgave 8.86 g

Sources & evidence

ORD record
ord-a3255638cfd041bb93ec4f0f7e1ef2bc
Source dataset
uspto-grants-1990_03
Patent number
USH0000753

Reaction notes

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