Sulfuric Acid → HCID 57173538, compound

HRID 127865Notes

Reaction equation

[O:1]=[C:2]([CH:4]=[C:5]([CH3:7])[CH3:6])[CH3:3].[CH3:8][C:9]([O:18][OH:19])([C:11]#[C:12][C:13]([CH3:17])([O:15][OH:16])[CH3:14])[CH3:10].S(=O)(=O)(O)O>CCOCC>[O:1]=[C:2]([CH2:4][C:5]([CH3:7])([CH3:6])[O:16][O:15][C:13]([CH3:17])([CH3:14])[C:12]#[C:11][C:9]([CH3:8])([CH3:10])[O:18][O:19][C:5]([CH3:7])([CH3:6])[CH2:4][C:2](=[O:1])[CH3:3])[CH3:3]

Participants

Conditions

Temperature: 30 °C

Procedure

A mixture of 19.6 g. (0.2 mole) of mesityl oxide, 74.4 g. (0.083 mole) of 2,5-dimethyl-2,5-dihydroperoxy-3-hexyne and 60 ml. of ether was stirred at 0° C. while 1.3 g. of 77% sulfuric acid solution was slowly added. The reaction mixture was allowed to warm slowly to 30° C. and stirred for a total of 16 hours. The organic layer was separated, washed with water, 5% sodium hydroxide solution and again with water to pH 8. The mixture was then subjected to steam distillation in the presence of sodium bicarbonate solution at 20 torr for 2 hours to remove unreacted mesityl oxide and hydroperoxide. The product was taken up in ether, dried over anhydrous magnesium sulfate and the ether removed under reduced pressure leaving 20.52 g. of product (66.7% yield).

Workup

additionA mixture of 19.6 g
customThe organic layer was separated
washwashed with water, 5% sodium hydroxide solution and again with water to pH 8
distillationThe mixture was then subjected to steam distillation in the presence of sodium bicarbonate solution at 20 torr for 2 hours
customto remove unreacted mesityl oxide and hydroperoxide
dry with materialdried over anhydrous magnesium sulfate
customthe ether removed under reduced pressure
customleaving 20.52 g

Sources & evidence

ORD record: ord-301dc6d3c2814b90a5b746ce9419eb71
Source dataset: uspto-grants-1981_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04257985

Reaction notes

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