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

HRID 1766918Notes

Reaction equation

HRID 1766918 reaction equation
[P:1]([O:11][CH2:12][C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:20][OH: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:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=1[C:20]([OH:24])=[O:21])([O:7][CH2:8][CH:9]=[CH2:10])=[O:2])[CH:5]=[CH2:6]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 17862639Diallyl 2-(hydroxymethyl)-6-methylbenzyl phosphateHCID 131709961Jones' reagent

Product 1

HCID 178624942-[[Bis(allyloxy)phosphoryl]oxymethyl]-3-methylbenzoic acidYield 71%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of diallyl 2-(hydroxymethyl)-6-methylbenzyl phosphate (1.22 g, 4.02 mmol) obtained from Example 22-(4) 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; 6 ml, ca. 16 mmol) was added thereto. The reaction mixture was stirred at room temperature for 2 hours, and then 2-propanol (1 ml) was added thereto to stop the reaction. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give an oily residue. The residue was dried using a vaccum pump, and then subjected to chromatography on a silica gel (50 g) column (eluent; ethyl acetate:dichloromethane=1:1) to afford the title compound (905.3 mg, 71% yield) as a colorless 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 dried

Sources & evidence

ORD record
ord-f0a6ff0fb27b453abe6355ef68f2adcc
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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