Bis(2-hydroxyethyl) terephthalate → Bis(2-hydroxyethyl) benzene-1,4-dicarboxylate;1-dichlorophosphoryloxyethane

HRID 2211569Notes

Reaction equation

[C:1]([O:15][CH2:16][CH2:17][OH:18])(=[O:14])[C:2]1[CH:13]=[CH:12][C:5]([C:6]([O:8][CH2:9][CH2:10][OH:11])=[O:7])=[CH:4][CH:3]=1.[P:19]([Cl:25])([Cl:24])(=[O:23])[O:20][CH2:21][CH3:22]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:6]([O:8][CH2:9][CH2:10][OH:11])(=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([C:1]([O:15][CH2:16][CH2:17][OH:18])=[O:14])=[CH:13][CH:12]=1.[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-ff882ee0868e4ce59fe63fc01d1ecae3
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101568B2

Reaction notes

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