Ethanol → (+)-1-[p-(4-Methylhexyl)anilino]-4-hydroxyanthraquinone

HRID 1075130

Reaction equation

Cl[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([OH:18])=[CH:4][CH:3]=1.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:26]([O-])(=O)[CH3:27].[Na+].C(O)C.[N+]([C:37]1[CH:42]=[CH:41]C=[CH:39][CH:38]=1)([O-])=O>C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:39][CH:38]([CH2:26][CH3:27])[CH2:37][CH2:42][CH2:41][C:23]1[CH:24]=[CH:25][C:20]([NH:19][C:2]2[C:15]3[C:14](=[O:16])[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[C:7](=[O:17])[C:6]=3[C:5]([OH:18])=[CH:4][CH:3]=2)=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1-Chloro-4-hydroxyanthraquinone (27.8 gm) is dissolved in 200 ml nitrobenzene in a boiling flask fitted with a stirrer and reflux condensor. After heating to 80° C., 18.1 gm (+)-4-methylhexyl)aniline, prepared according to Example 17, is added followed by the addition of 0.1 gm copper acetate and 20 gm sodium acetate. The mixture is stirred and heated to 150° C. for 4 hours. The mixture is then cooled to 80° C. and 500 ml ethanol is added. When cooled to room temperature the crude dye is separated by filtration, water and alcohol washed, and dried overnight. Chromatography on alumina using toluene as eluent affords the pure helichromic compound. The structure of the compound is confirmed by NMR.

Workup

customfitted with a stirrer
temperaturereflux condensor
additionis added
temperatureheated to 150° C. for 4 hours
temperatureThe mixture is then cooled to 80° C.
temperatureWhen cooled to room temperature the crude
customdye is separated by filtration, water and alcohol
washwashed
customdried overnight
customaffords the pure helichromic compound

Sources & evidence

ORD record: ord-5a552999306f466fa173de75f13ffa87
Source dataset: uspto-grants-1983_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04394070

Linked notes

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