Catechol → HCID 13253007, compound

HRID 2292382Notes

Reaction equation

HRID 2292382 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][CH2:21][CH3:22])=[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][CH2:21][CH3:22])=[O:17]

Participants

5

Reactant 3

HCID 289CatecholHCID 8471TriethylamineHCID 137039n-Butylphosphorodichloridate

Product 1

HCID 13253007HCID 13253007, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Pyrocatechol (0.993 g, 9.02 mM) was dissolved in 50 ml of ether and, using 1.825 g (18.04 mM) of triethylamine and 1.723 (9.02 mM) of n-butyl dichlorophosphate, the reaction was carried out at -5° C. to 0° C. and the reaction mixture treated in the same manner as in Reference Example 1. There was obtained 1.914 g (93.0% yield) of n-butyl o-phenylene phosphate as a colorless viscous oil. 1H-NMR(CDCl3) δ: 0.7~2.0(5H, m, C--CH2CH2CH3), 4.13 and 4.28(2H, each t, J=6.5 Hz, P--O--CH2), 7.10 (4H, s, ##STR64## Signals for trace amounts of ether and triethylamine were also observed.

Workup

  1. customwas carried out at -5° C. to 0° C.
  2. additionthe reaction mixture treated in the same manner as in Reference Example 1

Sources & evidence

ORD record
ord-2d93aa8acc4e448bb0e9c63d79e60dd2
Source dataset
uspto-grants-1989_01
Patent number
US04801703

Reaction notes

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