Phenol → t-Butyl phenol phenol
Reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC(=C)C>>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])([CH3:4])([CH3:2])[CH3:3].[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1Participants
4
Procedure
A mixture of tert-butyl phenol and phenol prepared by alkylating phenol with isobutylene to a C4 /phenol ratio of 0.25 to provide a t-butyl phenol/phenol mixture was flash distilled to remove color. The mixture had an average t-butyl:phenyl ratio of about 0.3 (about 25% phenol:75% t-butyl phenols). 360.7 grams of t-butyl phenols/phenol mixture was heated to 70°-75° C. under a nitrogen atmosphere and 137.3 grams (1.0 mole) of PCl3 was added dropwise at such a rate that excess reflux of PCl3 (b.p. 76° C.) did not occur. After completion of addition, the temperature was gradually elevated to 150° C. and held at that temperature for 1 hour after the reaction was completed. The heated reaction mixture was sparged with dry nitrogen to drive off any residual hydrogen chloride. Unreacted phenols were removed by distillation (about 32 grams). 319 grams of a phosphite mixture containing triphenyl and various t-butylphenyl/phenyl phosphites was obtained.