tert-Butanol → Isoxazolium, 2-(1,1-dimethylethyl)-5-methyl-, perchlorate (1:1)

HRID 972317Notes

Reaction equation

HRID 972317 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[CH:4][CH:3]=1.[C:7](O)([CH3:10])([CH3:9])[CH3:8].[Cl:12]([OH:16])(=[O:15])(=[O:14])=[O:13].O1CCCC1>CCOCC>[Cl:12]([O-:16])(=[O:15])(=[O:14])=[O:13].[C:7]([N+:5]1[O:6][C:2]([CH3:1])=[CH:3][CH:4]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8028TetrahydrofuranHCID 24247Perchloric AcidHCID 798335-Methylisoxazole

Product 1

HCID 151520Isoxazolium, 2-(1,1-dimethylethyl)-5-methyl-, perchlorate (1:1)

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1 kg. of 5-methylisoxazole and 892 g. of t-butanol were stirred under nitrogen at 0° C. and 6.37 kg. of 60% perchloric acid were slowly added over a 2 1/2 hour period with vigorous stirring at 0°-5° C. The resulting suspension was allowed to warm to room temperature and stirred overnight. The reaction mixture was then slowly added to a mixture of 20 l. of tetrahydrofuran and 10 l. of ether at 0°-10° C. over a 2 hr. period with stirring. The mixture was then cooled to -5° C. and stirred for an additional 2 hrs. The product (1.821 kg.) was washed well with ether, m.p. 120°-122° C. A second crop (171 g.) was obtained from the mother liquor, m.p. 118°-121° C.

Workup

  1. stirringstirred overnight
  2. additionThe reaction mixture was then slowly added to a mixture of 20 l
  3. stirringperiod with stirring
  4. temperatureThe mixture was then cooled to -5° C.
  5. stirringstirred for an additional 2 hrs
  6. washThe product (1.821 kg.) was washed well with ether, m.p. 120°-122° C
  7. customA second crop (171 g.) was obtained from the mother liquor, m.p. 118°-121° C.

Sources & evidence

ORD record
ord-1e46a59fa05b4fd3a7175f936f70d56e
Source dataset
uspto-grants-1977_10
Patent number
US04052510

Reaction notes

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