Phosphorus oxychloride → HCID 54161239, compound

HRID 484989Notes

Reaction equation

HRID 484989 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([CH3:10])=[CH:4][C:3]=1[CH:11]=[CH:12][C:13]([CH3:16])(O)[CH3:14].C[N+](C)=CCl.[Cl-].P(Cl)(Cl)(Cl)=O.[C:28]([O-])(=[O:30])C.[Na+]>CN(C)C=O>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([CH3:10])=[CH:4][C:3]=1[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:28]=[O:30]

Participants

6

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 517045Sodium AcetateHCID 54449301HCID 54449301, compound

Product 1

HCID 54161239HCID 54161239, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

4-(2,5-dimethyl-4-methoxyphenyl)-2-methyl-3-buten-2-ol (18 g, 0.08M) in 25 ml of N,N-dimethylformamide (DMF) was added dropwise at 0° C. (ice bath) to the Vilsmeier reagent prepared from 15.4 g of phosphorus oxychloride and 15 ml of DMF. The resulting mixture was heated slowly to 80° C. and was stirred at this temperature for 4 hrs. The content of reaction flask was poured into 250 ml of ice-water mixture and sodium acetate (80 g) was added slowly in portions. The product was then extracted into ether. After work-up, the residue was purified by a silica gel dry column (15% ethyl acetate in hexane) to give 12 g of pure material as yellow powder, m.p. 90°-92° C. MS(CI): 231(m+ +1).

Workup

  1. customThe content of reaction flask
  2. additionwas added slowly in portions
  3. extractionThe product was then extracted into ether
  4. customAfter work-up, the residue was purified by a silica gel
  5. dry with materialdry column (15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-9514510e17e54a1cbdea7109077aaf79
Source dataset
uspto-grants-1985_08
Patent number
US04534979

Reaction notes

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