3-Mercaptopropionic Acid → 10,10-Bis (p-hydroxyphenyl) anthrone

HRID 1109682Notes

Reaction equation

[CH:1]1[C:14]2[C:13](=O)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][CH:2]=1.S[CH2:18][CH2:19][C:20]([OH:22])=O>>[OH:16][C:6]1[CH:7]=[CH:12][C:13]([C:13]2([C:1]3[CH:18]=[CH:19][C:20]([OH:22])=[CH:3][CH:2]=3)[C:14]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6](=[O:16])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]2=3)=[CH:14][CH:5]=1

Participants

Reactant 2

HCID 65143-Mercaptopropionic Acid

HCID 6780Anthraquinone

Product 1

HCID 1230630510,10-Bis (p-hydroxyphenyl) anthrone

Conditions

Temperature: 65 °C

Procedure

Anthraquinone (60 g) phenol (150 g) and 3-mercaptopropionic acid (8 g) were placed in a round-bottom flask. The mixture was heated at 65° C., and then dry hydrogen chloride was bubbled in for about 24 h. The phenol, hydrogen chloride, and cocatalyst were removed by steam distillation. This product was recrystallized from methanol as a slightly yellowish granular mass: MP 320°-322° C.

Workup

customdry hydrogen chloride was bubbled in for about 24 h
customThe phenol, hydrogen chloride, and cocatalyst were removed by steam distillation
customThis product was recrystallized from methanol as a slightly yellowish granular mass

Sources & evidence

ORD record: ord-bf6541e73f954a91bdfead3f5efcdb04
Source dataset: uspto-grants-1994_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05322528

Reaction notes

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