Water → HCID 20734023, compound

HRID 353000Notes

Reaction equation

HRID 353000 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([C:7]([OH:9])=[O:8])=[CH:3][CH:2]=1.[CH2:25](O)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH:34]=[CH2:35].C(N([CH2:42][CH3:43])CC)C.O>S(Cl)(Cl)=O.ClCCl>[CH2:25]([O:8][C:7]([C:4]1[CH:5]=[CH:6][C:1]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([O:24][CH2:3][CH2:2][CH2:1][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:42]=[CH2:43])=[O:23])=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)=[CH:2][CH:3]=1)=[O:9])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH:34]=[CH2:35]

Participants

7

Reactant 4

HCID 962WaterHCID 818510-Undecen-1-olHCID 8471TriethylamineHCID 33698914-[4-(4-carboxyphenyl)phenyl]benzoic Acid

Product 1

HCID 20734023HCID 20734023, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A suspension of [1,1′;4′,1″]terphenyl-4,4″-dicarboxylic acid (6.37 g, 20 mmol) in 100 ml of thionyl chloride was heated at reflux for 12 h then thionyl chloride was evaporated by azeotropic distillation. The crude yellow residue obtained therefrom was mixed with 10-undecen-1-ol (7.49 g, 44 mmol) in dichloromethane (300 ml) and triethylamine (8.9 g, 88 mmol) was added dropwise to the resulting mixture. The reaction mixture was stirred at 6 h at room temperature, then poured into water (300 ml) and extracted with dichloromethane (2×400 ml). The combined organic extracts were washed with saturated NaCl solution (500 ml), dried over magnesium sulphate, filtered and evaporated to dryness to give a brownish residue which was recrystallised from acetone/dichlorometane: 9/1 to afford pure [1,1′;4′,1″]terphenyl-4,4″-dicarboxylic acid diundec-10-enyl ester as white crystalline material. Yield 8.97 g.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 h
  3. customthionyl chloride was evaporated by azeotropic distillation
  4. customThe crude yellow residue obtained
  5. additionwas added dropwise to the resulting mixture
  6. extractionextracted with dichloromethane (2×400 ml)
  7. washThe combined organic extracts were washed with saturated NaCl solution (500 ml)
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customto give a brownish residue which
  12. customwas recrystallised from acetone/dichlorometane

Sources & evidence

ORD record
ord-26920a0238a548b9b170a03db984eb32
Source dataset
uspto-grants-2004_06
Patent number
US06749771B1

Reaction notes

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