Dichloromethane → 2-Ethoxy-4,5-dihydro-5,5-dimethyl-2-oxo-1,3,2-benzodioxaphosphepin-7-yl methanesulphonate

HRID 27638

Reaction equation

HRID 27638 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([C:13]([CH3:17])([CH3:16])[CH2:14][OH:15])[CH:7]=1)(=[O:4])=[O:3].C(N(CC)CC)C.[P:25](Cl)(Cl)(=[O:29])[O:26][CH2:27][CH3:28].ClCCl>C(#N)C>[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]2[O:12][P:25]([O:26][CH2:27][CH3:28])(=[O:29])[O:15][CH2:14][C:13]([CH3:17])([CH3:16])[C:8]=2[CH:7]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 15158Ethyl dichlorophosphateHCID 233412804-Hydroxy-3-(2-hydroxy-1,1-dimethylethyl)phenyl methanesulphonate

Product 1

HCID 233412692-Ethoxy-4,5-dihydro-5,5-dimethyl-2-oxo-1,3,2-benzodioxaphosphepin-7-yl methanesulphonateYield 44.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Hydroxy-3-(2-hydroxy-1,1-dimethylethyl)phenyl methanesulphonate (10 g) from Example 1 was suspended in acetonitrile (100 ml) and triethylamine (8 g) was added. The mixture was cooled in ice, and ethyl phosphorodichloridate (6.9 g) was added dropwise with vigorous stirring. Stirring was continued for 6 hours prior to the addition of dichloromethane (200 ml), after which the solution was washed with water, dilute sodium hydroxide solution and water again, dried over magnesium sulphate and run down. The crude product was recrystallised from toluene, yielding 6.0 g of the desired product, melting point 113°-115° C.

Workup

  1. temperatureThe mixture was cooled in ice
  2. washafter which the solution was washed with water, dilute sodium hydroxide solution and water again
  3. dry with materialdried over magnesium sulphate
  4. customThe crude product was recrystallised from toluene

Sources & evidence

ORD record
ord-93e18560efd1442aa89ec305c02c79da
Source dataset
uspto-grants-1980_09
Patent number
US04222767

Linked notes

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