Pyridine → HCID 53875308, compound

HRID 1165723Notes

Reaction equation

HRID 1165723 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[Cl:23][C@@H:24]([CH:28]([CH3:30])[CH3:29])[C:25](Cl)=[O:26].C(Cl)(Cl)(Cl)[Cl:32]>>[Cl:23][C@H:24]([C:25]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:12]([Cl:32])=[O:14])=[CH:15][CH:16]=2)=[CH:6][CH:7]=1)=[O:26])[CH:28]([CH3:30])[CH3:29]

Participants

5

Reactant 4

HCID 1049PyridineHCID 5943Carbon Tetrachloride2×HCID 3015564'-Hydroxy-4-biphenylcarboxylic acidHCID 12239728HCID 12239728, compound

Product 1

HCID 53875308HCID 53875308, compound

Procedure

Three point five grams of 4-(4'-hydroxyphenyl)benzoic acid were dispersed in a mixed solvent of 30 ml of carbon tetrachloride and 5 ml of pyridine and then heated. 2.5 ml of (s)-2-chloro-3-methylbutanic acid chloride was dropped into the mixed solution with refluxing for 3 hours. After removing the solvent, a small amount of water was added to decompose unreacted nonanic acid chloride. (s)-4-(4'-(1-chloro-2-methylpropylcarbonyloxy)phenyl)benzoic acid (H) after washing the residue with methanol. 5 ml of thionylchloride was reacted with the compound (H) dispersed in 20 ml of carbon tetrachloride to obtain 6.5 g of (s)-4-(4'-(1-chloro-2-methylpropylcarbonyloxy)phenyl)benzoic acid chloride (I).

Workup

  1. temperatureheated
  2. temperaturewith refluxing for 3 hours
  3. customAfter removing the solvent
  4. additiona small amount of water was added
  5. wash(s)-4-(4'-(1-chloro-2-methylpropylcarbonyloxy)phenyl)benzoic acid (H) after washing the residue with methanol
  6. custom5 ml of thionylchloride was reacted with the compound (H)

Sources & evidence

ORD record
ord-12ca24b0e36947ac9b6ced5166fef503
Source dataset
uspto-grants-1990_03
Patent number
US04911861

Reaction notes

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