Hydrogen Peroxide → HCID 14010391, compound

HRID 2292195Notes

Reaction equation

[CH2:1]([C:5]1[CH:6]=[C:7]([CH:16]=[CH:17][C:18]=1[O:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9])[C:2](=[CH2:4])[CH3:3].B1C2CCCC1CCC2.[OH-].[Na+].OO.C(=O)([O-])[O-:40].[K+].[K+]>C1COCC1.O.C(O)C>[CH3:4][CH:2]([CH2:3][OH:40])[CH2:1][C:5]1[CH:6]=[C:7]([CH:16]=[CH:17][C:18]=1[O:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 15.0 g of 3-methallyl-4-pivaloyloxybenzophenone in 30 ml of THF was treated with 100 ml of 0.5M solution of 9-BBN in THF at 0° C. The mixture was stirred at 25° C. for 3 h and at 50° C. for 1 h. To the cooled reaction mixture were added 30 ml of ethanol, 9.5 ml of 6N sodium hydroxide, and 18 ml of 30% hydrogen peroxide. After stirring at 25° C. for 2 h, the oxidation mixture was treated with solid potassium carbonate followed by a small amount of water. The organic layer was separated and dried over MgSO4. The crude product (22 g) was chromatographed on a silica gel column using toluene-ethyl acetate. 8.0 g of product was obtained as an oil. Calcd. for C22H26O4 : C, 74.55; H, 7.39. Found: C, 74.30; H, 7.35.

Workup

customTo the cooled reaction mixture
stirringAfter stirring at 25° C. for 2 h
customThe organic layer was separated
dry with materialdried over MgSO4
customThe crude product (22 g) was chromatographed on a silica gel column

Sources & evidence

ORD record: ord-0d80c94822c04a4c8ddc456408c2c8d1
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04801610

Reaction notes

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