Hydrochloric Acid → HCID 178442826, compound

HRID 26235Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:25])[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].C(=O)([O-])[O-:27].[Na+].[Na+].OO.[OH-].[K+].Cl>C(O)C.O>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:25])[C:5]([OH:27])=[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: 50 °C

Procedure

A mixture of 1.7 parts of 5-chloro-2-dodecyl-1,4-naphthoquinone, 25 parts ethanol, 0.626 parts anhydrous sodium carbonate and 6.3 parts water was contacted with 1.13 parts of 30% hydrogen peroxide at 32° C. and then refluxed for 10 minutes. The resulting mixture was then cooled to 50° C. and a solution of 1.56 parts of potassium hydroxide in 49.5 parts of ethanol was added to it. The resulting deep red mixture was then heated to 50° C. over 25 minutes and the temperature held there for 45 minutes. After cooling to 10° C. the mixture was then contacted with 251 parts of 2.72% hydrochloric acid. The resulting yellow crystals were filtered, dried and purified by column chromatography on silica gel using 1-chlorobutane as eluent. Solvent removal gave 1.4 parts of 5-chloro-2-dodecyl-3-hydroxy-1,4-naphthoquinone, m.p. 102°-104.5° C.

Workup

temperaturerefluxed for 10 minutes
temperatureThe resulting deep red mixture was then heated to 50° C. over 25 minutes
temperatureAfter cooling to 10° C. the mixture
filtrationThe resulting yellow crystals were filtered
customdried
custompurified by column chromatography on silica gel
customSolvent removal

Sources & evidence

ORD record: ord-796b5c2ac47a4784958a99364585571e
Source dataset: uspto-grants-1979_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04148918

Reaction notes

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