Malonic Acid → HCID 220387, compound

HRID 2303465Notes

Reaction equation

HRID 2303465 reaction equation
[CH3:1][S:2]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(O)(=O)[CH2:14][C:15]([OH:17])=[O:16]>CCO.N1C=CC=CC=1>[CH3:1][S:2]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:14][C:15]([OH:17])=[O:16])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 867Malonic AcidHCID 2203764-(Methylsulfonyl)benzaldehyde

Product 1

HCID 220387HCID 220387, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 21975839Pyridine ethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of aldehyde 4-methylsulfonylbenzaldehyde 4 (1.0 g, 5.9 mmol) and malonic acid (0.63 g, 6.0 mmol) in 10:1 EtOH/pyridine (12.1 mL) was heated at a gentle reflux for 24 h. After cooling to 0° C., the resulting precipitate was collected and rinsed with cold Et2O. The solid was resuspended in EtOH (13 mL) and heated at reflux for an additional 2 h. After cooling to 0° C., the resulting precipitate was collected and dried in vacuo to afford 0.63 g (51%) of 3-(4-methanesulfonyl-phenyl)-acrylic acid 5 as a white solid; 1H NMR (DMSO) δ 3.18 (s, 3H), 6.65 (d, 1H, J=16.1), 7.60 (d, 1H, J=16.1), 7.89 (m, 4H).

Workup

  1. temperaturea gentle reflux for 24 h
  2. customthe resulting precipitate was collected
  3. washrinsed with cold Et2O
  4. temperatureheated
  5. temperatureat reflux for an additional 2 h
  6. temperatureAfter cooling to 0° C.
  7. customthe resulting precipitate was collected
  8. customdried in vacuo

Sources & evidence

ORD record
ord-37132efc8f954bb4b9a978af02c70f96
Source dataset
uspto-grants-2002_08
Patent number
US06433005B1

Reaction notes

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