Malonic Acid → (2E)-3-(4-((Methylsulfonyl)oxy)phenyl)-2-propenoic acid

HRID 2212033Notes

Reaction equation

HRID 2212033 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3](O)=O.C([C:10]1[CH:15]=[CH:14][C:13]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:12][CH:11]=1)=O.N1CCCCC1>N1C=CC=CC=1>[CH3:20][S:17]([O:16][C:13]1[CH:12]=[CH:11][C:10](/[CH:3]=[CH:2]/[C:1]([OH:7])=[O:6])=[CH:15][CH:14]=1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 144212934-Formylphenyl methanesulfonate

Product 1

HCID 15726601(2E)-3-(4-((Methylsulfonyl)oxy)phenyl)-2-propenoic acidYield 57.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

Malonic acid (7.80 g, 74.92 mmol) was added to a solution of the crude methanesulfonic acid 4-formylphenyl ester (10 g, 49.95 mmol), which was synthesized in the preceeding step, and piperidine (0.7 ml, 7.09 mmol) in pyridine (50 ml). The reaction mixture was heated to 90° C. for 2.5 h. It was cooled to room temperature. Concentrated hydrochloric acid/ice (400 ml/100 ml) was added. The precipitation was filtered off and washed with a 10% aqueous solution of acetic acid (200 ml). It was dried in vacuo to give 6.95 g of (E)-3-(4-(methanesulfonyloxy)phenyl)acrylic acid.

Workup

  1. temperatureIt was cooled to room temperature
  2. customThe precipitation
  3. filtrationwas filtered off
  4. washwashed with a 10% aqueous solution of acetic acid (200 ml)
  5. customIt was dried in vacuo

Sources & evidence

ORD record
ord-b2ff45cfe0f44c1dbf838bd196437a58
Source dataset
uspto-grants-2006_09
Patent number
US07101898B2

Reaction notes

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