Dimethylformamide → 2-(Acetoxymethyl)-5-[[bis(allyloxy)phosphoryl]oxymethyl]benzoyl chloride

HRID 1766860Notes

Reaction equation

[C:1]([O:4][CH2:5][C:6]1[CH:14]=[CH:13][C:12]([CH2:15][O:16][P:17]([O:23][CH2:24][CH:25]=[CH2:26])([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])=[CH:11][C:7]=1[C:8](O)=[O:9])(=[O:3])[CH3:2].C(Cl)(=O)C([Cl:30])=O.CN(C)C=O>O1CCCC1>[C:1]([O:4][CH2:5][C:6]1[CH:14]=[CH:13][C:12]([CH2:15][O:16][P:17]([O:23][CH2:24][CH:25]=[CH2:26])([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])=[CH:11][C:7]=1[C:8]([Cl:30])=[O:9])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

2-(Acetoxymethyl)-5-[[bis(allyloxy)phosphoryl]oxymethyl]benzoic acid (475.5 mg, 1.24 mmol) obtained from Example 1-(11) was dissolved in tetrahydrofuran (5 ml), and the solution was cooled to 0° C., then oxalyl chloride (189.2 mg, 1.49 mmol) and N,N-dimethylformamide (15 μl) were added thereto with stirring. The mixture was warmed to room temperature and then stirred for 40 minutes. The solvent was distilled off under reduced pressure to give the crude 2-(acetoxymethyl)-5-[[bis(allyloxy)phosphoryl]oxymethyl]benzoyl chloride.

Workup

temperatureThe mixture was warmed to room temperature
stirringstirred for 40 minutes
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-6db3acf9bea14bda995306ee62c393c1
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07230023B2

Reaction notes

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