tert-Butyl hydroperoxide → HCID 54457070, compound

HRID 1650032Notes

Reaction equation

[C:1]([O:22][CH:23]1[CH2:28][C:27]([CH3:30])([CH3:29])[NH:26][C:25]([CH3:32])([CH3:31])[CH2:24]1)(=[O:21])[C:2]1[CH:20]=[CH:19][CH:18]=[C:4]([C:5]([O:7][CH:8]2[CH2:13][C:12]([CH3:15])([CH3:14])[NH:11][C:10]([CH3:17])([CH3:16])[CH2:9]2)=[O:6])[CH:3]=1.[C:33]([O:37]O)([CH3:36])([CH3:35])C>[Mo](=O)(=O)=O.C1CCCCC1>[C:5]([O:7][CH:8]1[CH2:9][C:10]([CH3:17])([CH3:16])[N:11]([O:37][CH:33]2[CH2:36][CH2:18][CH2:4][CH2:5][CH2:35]2)[C:12]([CH3:14])([CH3:15])[CH2:13]1)(=[O:6])[C:4]1[CH:18]=[CH:19][CH:20]=[C:2]([C:1]([O:22][CH:23]2[CH2:24][C:25]([CH3:32])([CH3:31])[N:26]([O:37][CH:33]3[CH2:36][CH2:3][CH2:2][CH2:1][CH2:35]3)[C:27]([CH3:30])([CH3:29])[CH2:28]2)=[O:21])[CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 35.0 g (78.7 mmol) of di-(2,2,6,6-tetramethyl-piperidin-4-yl) isophthalate, 47.3 g (472 mmol) of 90% aqueous t-butyl hydroperoxide, 2.0 g of molybdenum trioxide, and 300 ml of cyclohexane is heated two hours at 140° C. in a Fischer-Porter bottle. The red reaction mixture is treated with an additional 20.0 g (90%, 200 mmol) of t-butyl hydroperoxide and heated at 140° C. for 120 minutes to discharge the red color. The reaction mixture is cooled, filtered, and the filtrate is evaporated to an oil which is crystallized from ethanol to afford 36.2 g (72% yield) of a white solid, m.p. 135°-141° C.

Workup

customThe red reaction mixture
temperatureheated at 140° C. for 120 minutes
temperatureThe reaction mixture is cooled
filtrationfiltered
customthe filtrate is evaporated to an oil which
customis crystallized from ethanol

Sources & evidence

ORD record: ord-61763392ab80444f9d502a4988e1710d
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04921962

Reaction notes

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