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

HRID 478121

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-eff9c98ac3f443f7a7ab079b0ea41b89
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06641833B2

Linked notes

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