2-Chloroethanol → 2-Chloroethyl perfluorooctanoate

HRID 1074264Notes

Reaction equation

[F:1][C:2]([F:25])([C:6]([F:24])([F:23])[C:7]([F:22])([F:21])[C:8]([F:20])([F:19])[C:9]([F:18])([F:17])[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[C:3](Cl)=[O:4].[Cl:26][CH2:27][CH2:28][OH:29]>>[F:1][C:2]([F:25])([C:6]([F:23])([F:24])[C:7]([F:21])([F:22])[C:8]([F:19])([F:20])[C:9]([F:17])([F:18])[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[C:3]([O:29][CH2:28][CH2:27][Cl:26])=[O:4]

Participants

Reactant 2

HCID 342-Chloroethanol

HCID 78978Perfluorooctanoyl chloride

Product 1

HCID 197517952-Chloroethyl perfluorooctanoate

Conditions

Temperature: 0 °C

Procedure

2-Chloroethyl perfluorooctanoate was prepared by adding 162 g (0.375 mol) of perfluorooctanoyl chloride to 32.2 g (0.40 mol) of 2-chloroethanol cooled at 0° C., stirring the resulting mixture at 0° for 2 h, and then stirring for about 2.5 days at 25°. Fractionation of the resulting solution gave 152.6 g (85% yield) of the chloroethyl ester, b.p. 84°-88° at 1.3 kpa (10 mm), 98% pure by GC. IR (CCl4): 2960 (sat'd CH), 1790 (C--O), 1300-1100 cm31 1 (CF, C-O). NMR (CCl4): 1H 4.59 (t, JHH 5.5 Hz, 2H, CH2) and 3.70 ppm (t, JHH 5.5 Hz, 2H, CH2); 19F -81.6 (t of t, JFF 10, 4 Hz, 3F, CF4), -119.0 (t of t, JFF 12, 6 Hz, 2, F, CF2C=O), -122.4 (m, 4F, CF2), -123.3 (m, 4F, CF2), and -126.8 ppm (m, 2F, CF2).

Workup

stirringstirring for about 2.5 days at 25°

Sources & evidence

ORD record: ord-8f040f1e656c4341ac7d4967f8829670
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04973714

Reaction notes

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