Hydrochloric Acid → HCID 19419403, compound

HRID 864610Notes

Reaction equation

HRID 864610 reaction equation
[CH2:1](I)[CH:2]=[CH2:3].[OH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([OH:20])=[O:19])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[OH-].[Na+].Cl>O.C(O)C>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([OH:20])=[O:19])=[CH:14][CH:13]=2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:13][CH2:12][CH2:9][CH2:10][CH2:11][CH2:6][CH:7]=[CH2:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11166Allyl iodideHCID 14798Sodium Hydroxide2×HCID 3015564'-Hydroxy-4-biphenylcarboxylic acid2×

Product 1

HCID 19419403HCID 19419403, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

All the five compounds were prepared by the same method. The compounds I-8, I-9, I-10, I-11 and I-12 were synthesized by separately reacting allyl iodide, compounds I-4, I-5, I-6 and I-7 with 4-hydroxybiphenyl-4'-carboxylic acid. The synthesis of compound I-12 was described below as an example. 3.62 g (0.0157 mole) 4-hydroxylbiphenyl-4'-carboxylic acid, 500 ml ethanol, 50 ml water, 0.5 g KI and 2.02 g (0.036 mole) NaOH were heated to reflux for one hour. 7 g compound I-7 was then added dropwise. The mixture was refluxed for 12 hours and then 100 ml of 10% NaOH aqueous solution was added. The mixture was again heated to reflux for 2 hours, and cooled to room temperature. Water and diluted HCl were poured into the cooled mixture to precipitate, and the precipitated white solid was filtered and recrystallized from acetic acid to obtain 4.43 g of white crystals. mp: I-8: 231.8° C.; I-9: 223.7° C.; I-10: 213.9° C.; I-11: 202.8° C.; I-12: 161.4° C. Yield: I-8: 66.9%;I-9: 84.03%; I-10: 81.4%; I-11: 89.96%; I-12: 80.6%. 1H-NMR:

Workup

  1. customAll the five compounds were prepared by the same method
  2. customThe synthesis of compound I-12
  3. temperatureto reflux for one hour
  4. temperatureThe mixture was refluxed for 12 hours
  5. temperatureThe mixture was again heated
  6. temperatureto reflux for 2 hours
  7. customto precipitate
  8. filtrationthe precipitated white solid was filtered
  9. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-13c557c7466d493f9fc744ca59e6b9a9
Source dataset
uspto-grants-1996_10
Patent number
US05563230

Reaction notes

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