Trifluoroacetic acid → 2-(Acetoxymethyl)-5-[[bis(allyloxy)phosphoryl]oxymethyl]benzoic acid

HRID 1766859Notes

Reaction equation

HRID 1766859 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:23]=[CH:22][C:21]([CH2:24][O:25][P:26]([O:32][CH2:33][CH:34]=[CH2:35])([O:28][CH2:29][CH:30]=[CH2:31])=[O:27])=[CH:20][C:7]=1[C:8]([O:10]CC1C=CC(OC)=CC=1)=[O:9])(=[O:3])[CH3:2].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[C:1]([O:4][CH2:5][C:6]1[CH:23]=[CH:22][C:21]([CH2:24][O:25][P:26]([O:32][CH2:33][CH:34]=[CH2:35])([O:28][CH2:29][CH:30]=[CH2:31])=[O:27])=[CH:20][C:7]=1[C:8]([OH:10])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 178625614-Methoxybenzyl 2-(acetoxymethyl)-5-[[bis(allyloxy)phosphoryl]oxymethyl]benzoate

Product 1

HCID 211104382-(Acetoxymethyl)-5-[[bis(allyloxy)phosphoryl]oxymethyl]benzoic acidYield 106.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-methoxybenzyl 2-(acetoxymethyl)-5-[[bis(allyloxy)phosphoryl]oxymethyl]benzoate (590.3 mg, 1.17 mmol) obtained from Example 1-(10) and anisole (600 mg, 5.55 mmol) was cooled to 0° C., and then trifluoroacetic acid (2 ml) was added thereto with stirring. The mixture was warmed to room temperature and allowed to stand for 20 minutes. The mixture was diluted with toluene and was concentrated under reduced pressure to eliminate the volatile components (repeated three times), and an aqueous solution of sodium hydrogen carbonate was added thereto, then the aqueous layer was washed with ethyl acetate. To the aqueous layer was added carefully a 2N aqueous solution of hydrochloric acid (10 ml), and the liberated carboxylic acid was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, and the solvent was distilled off under reduced pressure to afford the title compound (477.5 mg, quantitative yield) as a colorless oil.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. additionan aqueous solution of sodium hydrogen carbonate was added
  3. washthe aqueous layer was washed with ethyl acetate
  4. additionTo the aqueous layer was added carefully a 2N aqueous solution of hydrochloric acid (10 ml)
  5. extractionthe liberated carboxylic acid was extracted with ethyl acetate
  6. washThe extract was washed with a saturated aqueous solution of sodium chloride
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5cb1d2f20c914b7fa48228839adb2bc0
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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