Sodium Chloride → HCID 86592500, compound

HRID 1792420Notes

Reaction equation

HRID 1792420 reaction equation
[F:1][C:2]([F:47])([C:43]([F:46])([F:45])[F:44])[CH2:3][CH2:4][CH2:5][C:6]([CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]2[C:33]3[C:28](=[CH:29][C:30]([OH:34])=[CH:31][CH:32]=3)[O:27][CH2:26][C:25]2([C:36]2[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=2)[CH3:35])=[CH:20][CH:19]=1)(C(O)=O)[C:7]([OH:9])=[O:8].[Na+].[Cl-]>CS(C)=O>[OH:34][C:30]1[CH:29]=[C:28]2[C:33]([CH:24]([C:21]3[CH:22]=[CH:23][C:18]([O:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:6]([CH2:5][CH2:4][CH2:3][C:2]([F:47])([F:1])[C:43]([F:44])([F:45])[F:46])[C:7]([OH:9])=[O:8])=[CH:19][CH:20]=3)[C:25]([C:36]3[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=3)([CH3:35])[CH2:26][O:27]2)=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 5234Sodium ChlorideHCID 22033025HCID 22033025, compound

Product 1

HCID 86592500HCID 86592500, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of (4,4,5,5,5-pentafluoropentyl)(4-(4-(7-hydroxy-3-(4-hydroxyphenyl)-3-methylchroman-4-yl)phenyloxy)butyl)methane-1,1-dicarboxylic acid (0.19 g, 0.285 mmol) in dimethylsulfoxide (7.6 ml) was stirred at 125° C. for 3 hours. After the reaction was completed, the reaction mixture was treated with saturated NaCl solution and extracted with ethyl acetate:hexane=1:1. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to chromatography on silica gel (n-hexane:ethyl acetate=2:1) to give the title compound (0.12 g, 67.6%) as a white foamy solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-92e5dcd1589c4ee4b4d85ade5225b0e3
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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