Reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12]1(O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(C)C=CC=CC=1.S(Cl)(Cl)=O>CN(C)C=O>[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
154.1 g (1.0 mol) of 2,4-dihydroxybenzoic acid, 141.2 g (1.5 mol) of phenol, 500 ml of toluene and 1 ml of dimethylformamide are placed in a 1.5 l sulfonating flask fitted with stirrer, condenser, dropping funnel and gas outlet. 178.5 g (1.5 mol) of thionyl chloride are added dropwise over the course of 2.5 hours at an internal temperature of 100-105 C. The reddish, clear solution is then refluxed overnight (110-115 C.). Toluene and phenol are distilled off in vacuo, the highly viscous residue (271.5 g) is stirred in 300 ml of toluene/cyclohexane (7/3) and the mixture is left overnight to crystallize. The precipitate is filtered off with suction under cold conditions (10 C.) and the solid product is washed with 3×50 ml of toluene/cyclohexane (7/3) and then dried at 80 C. in vacuo, to give 125.5 g (54.4% of theory) of phenyl 2,4-dihydroxybenzoate (m.p. 135-137 C.).
Workup
- customfitted with stirrer, condenser
- temperatureThe reddish, clear solution is then refluxed overnight (110-115 C.)
- distillationToluene and phenol are distilled off in vacuo
- customto crystallize
- filtrationThe precipitate is filtered off with suction under cold conditions (10 C.)
- washthe solid product is washed with 3×50 ml of toluene/cyclohexane (7/3)
- customdried at 80 C
Sources & evidence
- ORD record
- ord-eb192bf2bcac41b3b20bf84db45f2a97
- Source dataset
- uspto-grants-1997_11
- Patent number
- US05688995
Linked notes
Loading…