Potassium Hydroxide → HCID 11022884, compound

HRID 2292818Notes

Reaction equation

[F:1][C:2]([F:21])([F:20])[C:3]1([C:16]([F:19])([F:18])[F:17])[O:7][C:6]([F:11])([CH2:8][CH2:9]I)[C:5]([F:15])([CH2:12][CH2:13]I)[O:4]1.[OH-].[K+]>>[F:19][C:16]([F:17])([F:18])[C:3]1([C:2]([F:1])([F:20])[F:21])[O:4][C:5]([F:15])([CH:12]=[CH2:13])[C:6]([F:11])([CH:8]=[CH2:9])[O:7]1

Participants

Reactant 2

HCID 14797Potassium Hydroxide

HCID 15686468HCID 15686468, compound

Product 1

HCID 11022884HCID 11022884, compoundYield 49.3%

Procedure

In a flask was charged 2,2-bis(trifluoromethyl)-4,5-difluoro-4,5-di(2-iodoethyl)-1,3-dioxolane (95 g, 017 mole), KOH (189 ml 10M, 1.89 mole) and phase transfer catalyst (Note) (24.6 g as 60% w/w aqueous solution, 0.034 mole). The reaction mixture was vigorously stirred at ambient temperature for 4 hrs. The bottom organic layer was separated and was further purified by distillation giving 25.0 g (49.3% yield) of the desired product obtained as a clear, colorless liquid, bp. 90° C./200 mm Hg. This product is a trans/cis isomeric mixture. The trans and cis isomers could be separated by distillation on a spinning-band column. 1H NMR (CDCl3): δ 5.90 (m, 2H), 5.70 (m, 4H) (trans isomer); 5.76 (m, 4H), 5.58 (m, 2H) (cis isomer); 19F NMR (CDCl3): -80.2 (m, 6F), -109.6 (m, 2F) (trans isomer); -80.2 (m, 3F), -81.0 (q, J=8.6 Hz, 3F),-109.3 (quintet, J=7.0 Hz, 2F).

Workup

customThe bottom organic layer was separated
distillationwas further purified by distillation

Sources & evidence

ORD record: ord-7c892dfb96c043049366e5f0c97f6601
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05684111

Reaction notes

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