Water → HCID 69503557, compound

HRID 397137Notes

Reaction equation

[P:1](Cl)([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:2].N12CCCN=C1CCCCC2.[C:29]1([CH2:35][CH:36]=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.O>C(Cl)Cl.CCOCC>[P:1]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([O:37][CH:36]=[CH:35][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

2-Phenylvinyl diphenyl phosphate was prepared by treating a solution of 4.6 mL (22 mmol) diphenyl chlorophosphate and 3.6 mL (24 mmol) 1,8-diazabicyclo[5.4.0]undec-7-ene in 20 mL methylene chloride 0° C. with 2.6 mL (20 mmol) phenylacetaldehyde (90% purity. The solution was stirred at 0° C. for 6 h, poured into a mixture of water and ether (75 mL each), and the organic phase was extracted twice with 0.1 N HCl (50 mL each) and then washed with brine (25 mL). The organic phase was then dried over MgSO4, filtered, and concentrated. Distillation using a Kugelrohr apparatus (225° C./0.1 torr) provided 6.4 g 2-phenylvinyl diphenyl phosphate (90% yield) as an approximately equal mixture of E and Z isomers.

Workup

custom2-Phenylvinyl diphenyl phosphate was prepared
extractionthe organic phase was extracted twice with 0.1 N HCl (50 mL each)
washwashed with brine (25 mL)
dry with materialThe organic phase was then dried over MgSO4
filtrationfiltered
concentrationconcentrated
distillationDistillation
customa Kugelrohr apparatus (225° C./0.1 torr)

Sources & evidence

ORD record: ord-6d1cd6dfb6644860bca614c3b5c59bc1
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06608212B1

Reaction notes

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