Benzaldehyde → HCID 59449617, compound

HRID 1875304Notes

Reaction equation

HRID 1875304 reaction equation
N1CCCCC1.[CH:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:15]([O:42][CH2:43][CH2:44][C:45]([F:63])([F:62])[C:46]([F:61])([F:60])[C:47]([F:59])([F:58])[C:48]([F:57])([F:56])[C:49]([F:55])([F:54])[C:50]([F:53])([F:52])[F:51])(=[O:41])[CH2:16][C:17]([O:19][CH2:20][CH2:21][C:22]([F:40])([F:39])[C:23]([F:38])([F:37])[C:24]([F:36])([F:35])[C:25]([F:34])([F:33])[C:26]([F:32])([F:31])[C:27]([F:30])([F:29])[F:28])=[O:18]>>[F:39][C:22]([F:40])([C:23]([F:37])([F:38])[C:24]([F:35])([F:36])[C:25]([F:33])([F:34])[C:26]([F:31])([F:32])[C:27]([F:28])([F:29])[F:30])[CH2:21][CH2:20][O:19][C:17](=[O:18])[C:16](=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:15]([O:42][CH2:43][CH2:44][C:45]([F:62])([F:63])[C:46]([F:60])([F:61])[C:47]([F:58])([F:59])[C:48]([F:57])([F:56])[C:49]([F:55])([F:54])[C:50]([F:53])([F:52])[F:51])=[O:41]

Participants

4

Reactant 3

HCID 240Benzaldehyde3×HCID 8082PiperidineHCID 59449615HCID 59449615, compound

Product 1

HCID 59449617HCID 59449617, compound

Procedure

In a 100 mL 3-neck flask, 0.7146 g of piperidine (8.358 mmol) catalyst, 1.4369 g of benzaldehyde (13.543 mmol), and 10.2061 g of bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) malonate (12.818 mmol) were stirred at room temperature. Throughout the reaction, both a solid and liquid were observed. After two hours, some of the liquid was removed mixed with acetone to obtain a GC sample that indicated a deficiency of benzaldehyde. Approximately 1 mL of additional benzaldehyde was added. After 24 hours, the reaction was stopped and solvent was removed on a rotary evaporator. The residue was dissolved in petroleum ether and cooled in dry ice overnight. The sample was then vacuum filtered to yield the desired white solid bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)2-benzylidenemalonate.

Workup

  1. customThroughout the reaction
  2. customsome of the liquid was removed
  3. additionmixed with acetone
  4. customto obtain a GC sample that
  5. waitAfter 24 hours
  6. customsolvent was removed on a rotary evaporator
  7. dissolutionThe residue was dissolved in petroleum ether
  8. temperaturecooled in dry ice overnight
  9. filtrationvacuum filtered

Sources & evidence

ORD record
ord-c492a9ddc4974a888e636fecddbc2628
Source dataset
uspto-grants-2012_11
Patent number
US08309376B2

Reaction notes

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