Hydrochloric Acid → 1,1,1-Trifluoro-2-decyl 4-(4'-decylbiphenyl-4-oxycarbonyl)-2,3,5,6-tetrafluorobenzoate

HRID 247793Notes

Reaction equation

HRID 247793 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([C:12](Cl)=[O:13])[C:8]([F:15])=[C:7]([F:16])[C:3]=1[C:4](Cl)=[O:5].[F:17][C:18]([F:30])([F:29])[C@H:19]([OH:28])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].CN(C1C=CC=CN=1)C.[CH2:40]([C:50]1[CH:55]=[CH:54][C:53]([C:56]2[CH:61]=[CH:60][C:59]([OH:62])=[CH:58][CH:57]=2)=[CH:52][CH:51]=1)[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49].Cl>C(N(CC)CC)C.C(Cl)Cl>[CH2:40]([C:50]1[CH:51]=[CH:52][C:53]([C:56]2[CH:61]=[CH:60][C:59]([O:62][C:4]([C:3]3[C:7]([F:16])=[C:8]([F:15])[C:9]([C:12]([O:28][CH:19]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:18]([F:29])([F:30])[F:17])=[O:13])=[C:10]([F:11])[C:2]=3[F:1])=[O:5])=[CH:58][CH:57]=2)=[CH:54][CH:55]=1)[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 218852-DimethylaminopyridineHCID 2779103(R)-1,1,1-Trifluorodecan-2-olHCID 132553402,3,5,6-Tetrafluorobenzene-1,4-dicarbonyl dichlorideHCID 150849074-(4-Decylphenyl)phenol

Product 1

HCID 542192141,1,1-Trifluoro-2-decyl 4-(4'-decylbiphenyl-4-oxycarbonyl)-2,3,5,6-tetrafluorobenzoateYield 41%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent2×

Procedure

To methylene chloride (20 ml) were added 2,3,5,6-tetrafluoroterephthalic acid chloride (0.27 g), (R)-(+)-1,1,1-trifluoro-2-decanol (0.1 g), triethylamine (0.05 g) and dimethylaminopyridine (0.02 g). After the mixture was left to stand for 8 hours in order to allow a reaction to proceed, 4-decyl-4'-hydroxybiphenyl (0.15 g) and triethylamine (0.05 g) were added thereto. The mixture was left for about 8 hours in order to allow a reaction to proceed, made acidic with 1N aqueous hydrochloric acid solution and extracted with methylene chloride. The extracted layer was washed with lN aqueous sodium carbonate solution, water, aqueous sodium chloride solution (saturated) and water, in this order, to make it neutral. The layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure in order to remove the solvent. The solid product obtained was purified by silica-gel column chromatography to obtain the titled compound (0.14 g).

Workup

  1. waitAfter the mixture was left
  2. customa reaction
  3. waitThe mixture was left for about 8 hours in order
  4. customa reaction
  5. extractionextracted with methylene chloride
  6. washThe extracted layer was washed with lN aqueous sodium carbonate solution, water, aqueous sodium chloride solution (saturated) and water, in this order
  7. dry with materialThe layer was dried over anhydrous magnesium sulfate
  8. distillationdistilled under reduced pressure in order
  9. customto remove the solvent
  10. customThe solid product obtained
  11. customwas purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-a685d9e6e30e4f4f9ba847fbf878c135
Source dataset
uspto-grants-1993_05
Patent number
US05207947

Reaction notes

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