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

HRID 1017107Notes

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-eae172f539294cb0bbf9ba5aa655dd80
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479067B2

Reaction notes

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