Acetic Acid → 5-Chloro-2-dodecyl-1,4-naphthoquinone

HRID 26234Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:7]2[OH:12].S(=O)(=O)(O)[OH:26].C(O)(=O)C.OO>C(Cl)Cl.O>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:26])[CH:5]=[C:6]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:7]2=[O:12]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 5.4 parts of 5-chloro-2-dodecyl-1-naphthalenol, 18 parts of 96% sulfuric acid, 71.5 parts of glacial acetic acid, and 29 parts of water was stirred at 70° C. and 8.85 parts of cold 30% hydrogen peroxide was added dropwise over 8 hours. Stirring at 70° C. was continued for another 17 hours. The mixture was cooled and an orange solid taken up in methylene chloride, and the extract washed with water, dried and stripped. The resulting tan solid was purified by column chromatography from 1-chlorotutane on silica gel to give 2 parts of 5-chloro-2-dodecyl-1,4-naphthoquinone, m.p. 57.5°-58.5° C.

Workup

stirringStirring at 70° C.
temperatureThe mixture was cooled
washthe extract washed with water
customdried
customThe resulting tan solid was purified by column chromatography from 1-chlorotutane on silica gel

Sources & evidence

ORD record: ord-3399aba7a90844738ae17448fc373466
Source dataset: uspto-grants-1979_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04148918

Reaction notes

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