Ethyl dichlorophosphate → 1,4-Bis(2-hydroxyethyl)cyclohexa-2,5-diene-1,4-dicarboxylate;1-dichlorophosphoryloxyethane

HRID 1862179Notes

Reaction equation

[OH:1][CH2:2][CH2:3][C:4]1([CH:15]=[CH:14][C:10]([CH2:16][CH2:17][OH:18])([C:11]([O-:13])=[O:12])[CH:9]=[CH:8]1)[C:5]([O-:7])=[O:6].[P:19]([Cl:25])([Cl:24])(=[O:23])[O:20][CH2:21][CH3:22]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[OH:1][CH2:2][CH2:3][C:4]1([CH:15]=[CH:14][C:10]([CH2:16][CH2:17][OH:18])([C:11]([O-:13])=[O:12])[CH:9]=[CH:8]1)[C:5]([O-:7])=[O:6].[P:19]([Cl:25])([Cl:24])(=[O:23])[O:20][CH2:21][CH3:22]

Participants

Conditions

Temperature: -40 °C

Procedure

Under an argon stream, 10 g of 1,4-bis(hydroxyethyl)terephthalate (BHET), 9.61 g of 4-dimethylaminopyridine (DMAP), and 70 mL of methylene chloride were placed in a 250 mL flask equipped with a funnel. The solution in the flask was cooled down to −40° C. with stirring, and a solution of 5.13 g of ethyl phosphorodichloridate (EOP) (distilled before use) in 20 mL of methylene chloride was added dropwise through the funnel. After addition was complete, the mixture was stirred at room temperature for four hours to form the homopolymer BHET-EOP.

Workup

customequipped with a funnel
additionAfter addition
stirringthe mixture was stirred at room temperature for four hours

Sources & evidence

ORD record: ord-66b3f56ab27c4ca0a8585b8feeed81f5
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06537585B1

Reaction notes

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