Sulfuric Acid → HCID 178442822, compound

HRID 1111471Notes

Reaction equation

CN[CH:3]([C:15]1[C:16](=[O:27])[C:17]2[C:22]([C:23](=[O:26])[C:24]=1[OH:25])=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].S(=O)(=O)(O)O>C1(C)C(C)=CC=CC=1>[CH:3]([C:15]1[C:16](=[O:27])[C:17]2[C:22]([C:23](=[O:26])[C:24]=1[OH:25])=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

Conditions

Temperature: 120 °C

Procedure

Into a 30 ml glass autoclave, 1.00 g (2.67 mmol) of 2-(1-methylaminododecyl)-3-hydroxy-1,4-naphthoquinone, 305.6 mg (1.1 mmol times relative to the starting material) of concentrated sulfuric acid and 20 ml of xylene were charged, then heated to 120° C. under stirring and maintained at that temperature for one hour. The mixture was left to cool and then extracted with a benzene/water system. The organic layer was dried over sodium sulfate, and the solvent was distilled off. The residue was recrystallized from methanol to obtain 734.6 mg of 2-(1-dodecenyl)-3-hydroxy-1,4-naphthoquinone. Further, the filtrate of the recrystallization was analyzed by HPLC, whereby it was confirmed that the filtrate contained 12.4 mg of 2-hydroxy-1,4-naphthoquinone, 0.7 mg of the starting material and 15.5 mg of the desired product. The yield, etc. are shown in Table 3.

Workup

temperaturemaintained at that temperature for one hour
waitThe mixture was left
temperatureto cool
extractionextracted with a benzene/water system
dry with materialThe organic layer was dried over sodium sulfate
distillationthe solvent was distilled off
customThe residue was recrystallized from methanol

Sources & evidence

ORD record: ord-cc935a2b785040ccb5174ed776d62b19
Source dataset: uspto-grants-1990_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04980489

Reaction notes

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