Benzene → 2,2,3,4,4,4-Hexafluorobutyl 11-bromoundecylate

HRID 2071915

Reaction equation

HRID 2071915 reaction equation
[F:1][C:2]([F:11])([CH:5]([F:10])[C:6]([F:9])([F:8])[F:7])[CH2:3][OH:4].[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](O)=[O:24].CS(O)(=O)=O.C1C=CC=CC=1>O>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:4][CH2:3][C:2]([F:11])([F:1])[CH:5]([F:10])[C:6]([F:9])([F:7])[F:8])=[O:24]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6395Methanesulfonic AcidHCID 1781211-Bromoundecanoic acidHCID 5339902,2,3,4,4,4-Hexafluorobutan-1-ol

Product 1

HCID 214099962,2,3,4,4,4-Hexafluorobutyl 11-bromoundecylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 500 ml one-necked flask fitted with a Dean Stark trap was charged with 36.4 g (0.2 m) of 2,2,3,4,4,4-hexafluorobutanol, 53.0 g (0.2 m) of 11-bromoundecanoic acid, 0.5 g methane sulfonic acid and 100 ml of dry benzene. The reaction mixture was refluxed until the theoretical amount of water, 3.6 ml, was removed. The reaction mixture was washed with a 10% sodium carbonate solution. The benzene was removed under vacuum giving 2,2,3,4,4,4-hexafluorobutyl 11-bromoundecylate. IR analysis showed the following major absorption bands: 2930, 2860, 1760, 1190, 1110 cm-1.

Workup

  1. customA 500 ml one-necked flask fitted with a Dean Stark trap
  2. customwas removed
  3. washThe reaction mixture was washed with a 10% sodium carbonate solution
  4. customThe benzene was removed under vacuum

Sources & evidence

ORD record
ord-06b9c2b14c4f4c74ab72adb7a57f7125
Source dataset
uspto-grants-1977_09
Patent number
US04049668

Linked notes

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