Decane, 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-iodo- → 1,1,2,2-Tetrahydroperfluorodecanethiol

HRID 1936976

Reaction equation

HRID 1936976 reaction equation
N[C:2](N)=[S:3].[F:5][C:6]([F:32])([CH2:29]CI)[C:7]([F:28])([F:27])[C:8]([F:26])([F:25])[C:9]([F:24])([F:23])[C:10]([F:22])([F:21])[C:11]([F:20])([F:19])[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14]>C(O)C>[F:5][C:6]([F:32])([CH2:29][CH2:2][SH:3])[C:7]([F:27])([F:28])[C:8]([F:25])([F:26])[C:9]([F:23])([F:24])[C:10]([F:21])([F:22])[C:11]([F:20])([F:19])[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14]

Participants

4

Reactant 2

HCID 74885Decane, 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-iodo-HCID 2723790Thiourea

Product 1

HCID 5427551,1,2,2-TetrahydroperfluorodecanethiolYield 93.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of thiourea (105.7 g, 1.39 moles), 2-(perfluorooctyl)ethyl iodide (531.5 g), 0.926 moles) and anhydrous ethanol (1000 mL) was heated at reflux for 6 hours. Approximately half of the alcohol was removed at reduced pressure and replaced with water. Solid sodium hydroxide (37.0 g) was added and the mixture heated under slow nitrogen purge. The volatile liquid products were collected by steam distillation using a modified Dean-Stark apparatus to yield 414 g (93.1 molar yield) of 2-(perfluorooctyl)ethyl mercaptan. After two consecutive water washes the product was suficiently pure by glc (99.3%) and used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. customApproximately half of the alcohol was removed at reduced pressure
  4. additionSolid sodium hydroxide (37.0 g) was added
  5. temperaturethe mixture heated under slow nitrogen
  6. custompurge
  7. distillationThe volatile liquid products were collected by steam distillation

Sources & evidence

ORD record
ord-8992845735af4df482151e6c00fc53ea
Source dataset
uspto-grants-2002_05
Patent number
US06391948B1

Linked notes

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