Carbon Dioxide → HCID 69801495, compound

HRID 2184216Notes

Reaction equation

HRID 2184216 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3](O)=O.C([C:10]1[CH:25]=[CH:24][C:13]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])=[CH:12][CH:11]=1)=O.N1CCCCC1.C(=O)=O>N1C=CC=CC=1.O>[CH2:17]([O:16][C:14]([C:13]1[CH:24]=[CH:25][C:10]([CH:3]=[CH:2][C:1]([OH:7])=[O:6])=[CH:11][CH:12]=1)=[O:15])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 867Malonic AcidHCID 8082PiperidineHCID 11528845Benzyl 4-formylbenzoate

Product 1

HCID 69801495HCID 69801495, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

245 g (2.4 mol) of malonic acid were dissolved in 360 ml of pyridine (exothermic, temperature raised to about 50° C.). Then 503 g of the crude benzyl 4-formylbenzoate obtained in step a) and 20 ml of piperidine were added, and the mixture was heated to reflux until the production of carbon dioxide had ceased (about 7 h). The mixture was cooled to room temperature, then 2 l of water were added and the product was precipitated by acidification of the stirred mixture with ca. 600 ml of concentrated hydrochloric acid to pH 1.8 at 10° C. The precipitated product was filtered off, washed with water and dried at 50° C. under reduced pressure. Combined yield of step a) and step b): 529.1 g (97%).

Workup

  1. temperaturethe mixture was heated
  2. custom(about 7 h)
  3. customthe product was precipitated by acidification of the stirred mixture with ca. 600 ml of concentrated hydrochloric acid to pH 1.8 at 10° C
  4. filtrationThe precipitated product was filtered off
  5. washwashed with water
  6. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-eb2b59d9d8d14beb9d6f8e8fd4cc2e58
Source dataset
uspto-grants-2005_05
Patent number
US06900318B1

Reaction notes

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