Thymol → Bis(2-isopropyl-5-methylphenyl) chlorothiophosphate

Reaction equation

[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[OH:11])([CH3:3])[CH3:2].[H-].[Na+].[P:14]([Cl:18])(Cl)(Cl)=[S:15]>>[P:14]([Cl:18])([O:11][C:5]1[CH:6]=[C:7]([CH3:10])[CH:8]=[CH:9][C:4]=1[CH:1]([CH3:3])[CH3:2])([O:11][C:5]1[CH:6]=[C:7]([CH3:10])[CH:8]=[CH:9][C:4]=1[CH:1]([CH3:3])[CH3:2])=[S:15]

Participants

Reactant 3

HCID 6989Thymol

HCID 19883Thiophosphoryl chloride

HCID 24758Sodium hydride

Product 1

HCID 19690221Bis(2-isopropyl-5-methylphenyl) chlorothiophosphateYield 63%

Procedure

2-isopropyl-5-methylphenol was reacted with sodium hydride and thiophosphoryl chloride using the procedure of Example 21 to form bis(2-isopropyl-5-methylphenyl) chlorothiophosphate (31PNMR, singlet, 57 ppm). This compound was reacted with diphenylphosphonothioic amide by the General Method C(ii) (THF) yielding the compound of Formula I in which R1 =R2 =phenyl and R3 =R4 =2-isopropyl-5-methylphenoxy. Yield 63%; titration purity, 90%, MW593; 31PNMR, quartet 53 ppm. Test 2 (Table 2) showed that the product is a very strong extractant for zinc; however on long standing it crystallised from ESCAID solution.