Hydrochloric Acid → HCID 67285452, compound

HRID 1943535Notes

Reaction equation

HRID 1943535 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[OH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[CH:14]=2)=[CH:9][CH:8]=1.C(N([CH2:31][CH3:32])CC)C.Cl.[OH-:34].[Na+].Cl[CH2:37]Cl>C(C1C(O)=C(C(C)(C)C)C=C(C)C=1)(C)(C)C.O>[C:37]([O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([O:25][C:1](=[O:4])[CH:2]=[CH2:3])=[CH:21][CH:20]=3)[CH:14]=2)=[CH:11][CH:12]=1)(=[O:34])[CH:31]=[CH2:32]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 14798Sodium HydroxideHCID 667696[1,1';3',1'']Terphenyl-4,4''-diol

Product 1

HCID 67285452HCID 67285452, compound

Reagents, catalysts & solvents 2

HCID 314042,6-Di-tert-butyl-4-methylphenolCatalystHCID 962WaterSolvent2×

Procedure

Acryloyl chloride (8.97 g, 99.1 mmol) was added dropwise to a mixture of dichloromethane (100 mL), the compound (T-8) (10.0 g, 38.1 mmol), triethylamine (10.0 g, 99.1 mmol) and 2,6-di-tert-butyl-p-cresol (8.4 mg, 0.0381 mmol) in an ice bath under an atmosphere of nitrogen, and then the mixture was warmed slowly to room temperature. The stirring was continued at room temperature for 16 hours, and the reaction mixture was poured into water. The organic layer was wished with 1M-hydrochloric acid, aqueous 1M-sodium hydroxide solution and water. After the organic layer had been dried over anhydrous magnesium sulfate, the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: toluene), and then by recrystallization from a mixed solvent of ethanol and ethyl acetate to give colorless crystals (4.73 g) of 4,4″-bis(acryloyloxy)-(1,1′:3′,1″)-terphenyl (1-2-33).

Workup

  1. dry with materialAfter the organic layer had been dried over anhydrous magnesium sulfate
  2. distillationthe organic solvent was distilled off under reduced pressure
  3. customThe residue was purified by silica gel chromatography (eluent: toluene)
  4. customby recrystallization from a mixed solvent of ethanol and ethyl acetate

Sources & evidence

ORD record
ord-26b8c37b5a0c4d6a9718589da929de37
Source dataset
uspto-grants-2013_03
Patent number
US08394468B2

Reaction notes

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