4-Aminophenol → 4-Amino-4'-hydroxybiphenyl
Reaction equation
C1[C:6]([NH2:7])=[CH:5][CH:4]=C(O)C=1.O=[C:10]([CH2:16][CH2:17][C:18](O)=O)[CH2:11][CH2:12][C:13](O)=[O:14].O1C2(CCC(=O)O2)C[CH2:23][C:22]1=O>>[NH2:7][C:6]1[CH:5]=[CH:4][C:16]([C:10]2[CH:11]=[CH:12][C:13]([OH:14])=[CH:23][CH:22]=2)=[CH:17][CH:18]=1Participants
Procedure
The hydroxy-containing primary amino compound and the spirodilactam precursor are typically contacted in a molar ratio of about 2:1 in the presence of an inert reaction diluent capable of dissolving at least a portion of each reactant at reaction temperature. A preferred class of reaction diluents comprises N-alkylamides such as N,N-dimethylacetamide or N-methyl-2-pyrrolidone. Reaction conditions include a reaction temperature from about 80° C. to about 200° C. and a reaction pressure sufficient to maintain the reaction mixture in the liquid phase. Such pressures are from about 0.8 atmosphere to about 20 atmospheres. Subsequent to reaction, the hydroxyaryl-substituted spirodilactam is recovered, if desired, by conventional methods such as extraction, solvent removal and precipitation. The isolation of the hydroxyaryl-substituted spirodilactam is not required, however, and the spirodilactam is further reacted in situ to form the cyanato derivative without isolation. By way of specific illustration, p-aminophenol reacts with either 4-oxoheptanedioic acid or 1,6-dioxaspiro[4.4]nonane-2,7-dione to produce 1,6-di(4-hydroxyphenyl)-1,6-diasaspiro[4.4]nonane-2,7-dione and 4-amino-4'-hydroxybiphenyl reacts with either di(2-carboxyphenyl)ketone or 3,4,8,9-dibenzo-1,6-dioxaspiro[4.4]nonane-2,7-dione to produce 1,6-di[4-(4'-hydroxybiphenyl)]-3,4,8,9-dibenzo-1,6diasaspiro[4.4]nonane-2,7-dione.
Sources & evidence
- ORD record
- ord-3926edc4c7ae4ff786ac49f6bca6968f
- Source dataset
- uspto-grants-1990_05
- Patent number
- US04927908
Reaction notes
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