Carbon Dioxide → 3-(4-Pentafluorosulfanyl-phenyl)-acrylic Acid

HRID 854696Notes

Reaction equation

HRID 854696 reaction equation
[F:1][S:2]([F:14])([F:13])([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.C(O)(=O)[CH2:16][C:17]([OH:19])=[O:18].N1CCCCC1.C(=O)=O.Cl>N1C=CC=CC=1>[F:1][S:2]([F:14])([F:13])([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH:16][C:17]([OH:19])=[O:18])=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 27792074-(Pentafluoro-lambda6-sulfanyl)benzaldehyde

Product 1

HCID 740695713-(4-Pentafluorosulfanyl-phenyl)-acrylic Acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 5.40 g (23.3 mmol) 4-pentafluorosulfanyl-benzaldehyde, 2.42 g (23.3 mmol) malonic acid, 0.20 g (2.3 mmol) piperidine and 10.0 ml pyridine was kept at reflux temperature until carbon dioxide development ceased (4 h). The reaction mixture was poured into a solution of 100 ml ice and 60 ml 6N HCl. The precipitate was isolated, washed with water, then with n-heptane and dried in vacuum at 40° C. Yield: 5.73 g (90%) 3-(4-pentafluorosulfanyl-phenyl)-acrylic acid.

Workup

  1. custom(4 h)
  2. customThe precipitate was isolated
  3. washwashed with water
  4. dry with materialwith n-heptane and dried in vacuum at 40° C

Sources & evidence

ORD record
ord-101ba627392f4753956b1225d24ec365
Source dataset
uspto-grants-2007_08
Patent number
US07259262B2

Reaction notes

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