Sodium Hydroxide → 5-Benzyl-3-dodecylisoxazole

HRID 264111Notes

Reaction equation

C1(CC(=O)CC(=O)CC)C=CC=CC=1.Cl.[NH2:16][OH:17].[OH-].[Na+].[CH2:20]([C:32]1ON=[C:34]([CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:33]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>C(O)(=O)C>[CH2:20]([C:32]1[CH:33]=[C:34]([CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[O:17][N:16]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 1-phenyl-2,4-hexanedione (66.5 g, 0.201 mol), hydroxylamine hydrochloride (27.9 g, 0.402 mol), and 1M sodium hydroxide (201 mL, 0.201 mol) in glacial acetic acid (1.5 L) was stirred at 65° C. under nitrogen for 23 hours. The solution was allowed to cool, and the resulting suspension was filtered off and washed with CH3CO2H--H2O (9:1). The filtercake was washed separately with H2O and dried under house vacuum/air stream to give a white crystalline solid containing the title compound and 5-dodecyl-3-(phenylmethyl)isoxazole; yield 41.8 g (64%); mp 41°-43° C. Additional product was obtained by reheating the CH3CO2H filtrate and washings to 60° C.; adding H2O (150 mL) dropwise until cloudy, and following the previous procedure; yield 15.2 g (23%).

Workup

temperatureto cool
filtrationthe resulting suspension was filtered off
washwashed with CH3CO2H--H2O (9:1)
washThe filtercake was washed separately with H2O
customdried under house vacuum/air stream
customto give a white crystalline solid

Sources & evidence

ORD record: ord-14b1eaf72049447e8c117bb8244e7965
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05646170

Reaction notes

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