Hydrochloric Acid → HCID 131735800, compound

HRID 2204898Notes

Reaction equation

HRID 2204898 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10](O)(=O)[CH2:11][C:12]([OH:14])=[O:13].N1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.N1C=CC=CC=1.Cl>>[C:12]([O-:14])(=[O:13])[CH:11]=[CH:6][C:5]1[CH:8]=[CH:9][CH:2]=[CH:3][CH:4]=1.[CH3:10][C:11]12[CH2:12][CH:20]([CH2:21][CH2:22]1)[CH:19]=[CH:18]2

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 1049PyridineHCID 8082PiperidineHCID 680234-Fluorobenzaldehyde

Product 1

HCID 131735800HCID 131735800, compoundYield 72%

Procedure

17.1 g (0.138 mol) of 4-fluorobenzaldehyde, 28.7 g (0.276 mol) of malonic acid, and 0.1 equivalent of piperidine were dissolved in 3 equivalents of pyridine. The resulting mixture was stirred at room temperature for 30 min, and further stirred at 90° C. for 5 h. The temperature was lowered to room temperature, and the mixture was titrated to pH 1˜2 using a 3 M hydrochloric acid aqueous solution. The formed powder was filtered, and washed with a solvent mixture of ethanol/water (1/9 volume ratio), thus obtaining poly(cinnamate-methyl-2-norbornene) at a yield of 72% with a weight average molecular weight of 703,000 and PDI of 2.0.

Workup

  1. stirringfurther stirred at 90° C. for 5 h
  2. customwas lowered to room temperature
  3. filtrationThe formed powder was filtered
  4. washwashed with a solvent mixture of ethanol/water (1/9 volume ratio)

Sources & evidence

ORD record
ord-01d0fa581df94ef4a884b880778cad20
Source dataset
uspto-grants-2016_06
Patent number
US09366907B2

Reaction notes

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