Phenol → 7-Hydroxy-9,9-dimethylacridin-2(9H)-one

HRID 865627Notes

Reaction equation

HRID 865627 reaction equation
C1(O)C=CC=CC=1.C1C2CC3C(=CC=CC=3)NC=2C=CC=1.OC1C[CH2:27][C:26]2([C:41]3[C:36]([CH:37]=[CH:38][C:39](=[O:42])[CH:40]=3)=[N:35][C:34]3[C:29]2=[CH:30][C:31]([OH:43])=[CH:32][CH:33]=3)[CH2:25]C1.C1(C2(C3C=CC=CC=3)C3C(C=CC(=O)C=3)=NC3C2=CC(O)=CC=3)C=CC=CC=1>S(=O)(=O)(O)O>[CH3:25][C:26]1([CH3:27])[C:41]2[C:36]([CH:37]=[CH:38][C:39](=[O:42])[CH:40]=2)=[N:35][C:34]2[C:29]1=[CH:30][C:31]([OH:43])=[CH:32][CH:33]=2

Participants

6

Reactant 4

HCID 996PhenolHCID 7106Acridan3×HCID 54349067HCID 54349067, compoundHCID 57242337HCID 57242337, compound

Product 1

HCID 151094387-Hydroxy-9,9-dimethylacridin-2(9H)-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Hill et al., The Phenol Dyestuff of Liehermann as an Acridan Derivative, J. Chem. Soc. (C) 2462 (1970), describes an acridan derivative, 7-hydroxyspiro [acridine-9,1'-cyclohexa-2', 5'-diene]-2(9H), 4'-dione, that has been used as an oxidation-reduction indicator. This compound and related acridan derivatives, 4',7-dihydroxyspiro [acridine-9,1'-cyclohexane]-2(9H)-one; 7-hydroxy-2',3',5',6'-tetramethylspiro[acridine-9,1'-cyclohexa-2', 5'-diene]-2(9H), 4'-dione; 9,9-diphenyl-7-hydroxyacridin-2 (9H)-one; and 9,9-dimethyl-7-hydroxyacridin-2(9H)-one, yield blue solutions in sulfuric acid which turn red on dilution, this color being due to protonation of the free base. The neutral forms of the compounds are yellow in most solvents. A method of synthesizing these compounds is also disclosed.

Sources & evidence

ORD record
ord-4e921e4b75a74d62802b36cedbc2c26b
Source dataset
uspto-grants-1996_10
Patent number
US05567624

Reaction notes

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