Catechol → 2-Propoxy-2H-1,3,2lambda~5~-benzodioxaphosphol-2-one

HRID 236212Notes

Reaction equation

HRID 236212 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].C(N(CC)CC)C.[P:16](Cl)(Cl)([O:18][CH2:19][CH2:20][CH3:21])=[O:17]>CCOCC>[P:16]1([O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:1]=2[O:2]1)([O:18][CH2:19][CH2:20][CH3:21])=[O:17]

Participants

5

Reactant 3

HCID 289CatecholHCID 8471TriethylamineHCID 517771Phosphorodichloridic acid, propyl ester

Product 1

HCID 157008312-Propoxy-2H-1,3,2lambda~5~-benzodioxaphosphol-2-oneYield 101.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Pyrocatechol (0.856 g, 7.77 mM) was dissolved in 32 ml of ether and, using 1.573 g (15.54 mM) of triethylamine and 1.484 g (7.77 mM) of n-propyl dichlorophosphate, the reaction was carried out at -30° C. to -25° C. and the reaction mixture treated in the same manner as in Reference Example 1. There was obtained 1.695 g (95.6% yield) of n-propyl o-phenylene phosphate as a viscous oil (slightly turbid).

Workup

  1. customwas carried out at -30° C. to -25° C.
  2. additionthe reaction mixture treated in the same manner as in Reference Example 1

Sources & evidence

ORD record
ord-7bc211a2e0874192b5ff4cfb72378056
Source dataset
uspto-grants-1987_02
Patent number
US04642365

Reaction notes

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