Sulfuric Acid → 2-[[Bis(allyloxy)phosphoryl]oxymethyl]-3-chlorobenzoic acid

HRID 1766931Notes

Reaction equation

HRID 1766931 reaction equation
[P:1]([O:11][CH2:12][C:13]1[C:18]([CH2:19][OH:20])=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:21])([O:7][CH2:8][CH:9]=[CH2:10])([O:3][CH2:4][CH:5]=[CH2:6])=[O:2].CC(C)=[O:24].OS(O)(=O)=O.O=[Cr](=O)=O.S(=O)(=O)(O)O.CC(O)C>CC(C)=O.O>[CH2:4]([O:3][P:1]([O:11][CH2:12][C:13]1[C:14]([Cl:21])=[CH:15][CH:16]=[CH:17][C:18]=1[C:19]([OH:24])=[O:20])([O:7][CH2:8][CH:9]=[CH2:10])=[O:2])[CH:5]=[CH2:6]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 17862563Diallyl 2-chloro-6-(hydroxymethyl)benzyl phosphateHCID 131709961Jones' reagent

Product 1

HCID 178625562-[[Bis(allyloxy)phosphoryl]oxymethyl]-3-chlorobenzoic acidYield 76%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of diallyl 2-chloro-6-(hydroxymethyl)benzyl phosphate (2.62 g, 7.88 mmol) obtained from Example 27-(3) in acetone (25 ml) was cooled to 0° C., and Jones reagent (a mixture of chromic anhydride (5.34 g) and concentrated sulfuric acid (4.6 ml) diluted with water to 20 ml total volume; 12 ml, ca. 32 mmol) was added thereto. The reaction mixture was stirred at room temperature for 1 hour, and then 2-propanol (1 ml) was added thereto to stop the reaction. The insoluble material was filtered off, and then the filtrate was concentrated under reduced pressure to give an oily residue. The residue was thoroughly dried using a vaccum pump, and then subjected to chromatography on a silica gel (40 g) column (eluent; ethyl acetate:dichloromethane=1:10˜1:1) to afford the title compound (2.065 g, 76% yield) as a pale brown oil.

Workup

  1. additionwas added
  2. customthe reaction
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customto give an oily residue
  6. customThe residue was thoroughly dried

Sources & evidence

ORD record
ord-f8a8e422ee3149f6885e54df0e041c4a
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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