Malonic Acid → (E)-3-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)acrylic acid

HRID 342098

Reaction equation

HRID 342098 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH:11]=O)[C:5]=2[O:4][CH2:3][CH2:2]1.C(O)(=O)[CH2:14][C:15]([OH:17])=[O:16].N1CCCC1>N1C=CC=CC=1>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10](/[CH:11]=[CH:14]/[C:15]([OH:17])=[O:16])[C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 31268PyrrolidineHCID 27950332,3-Dihydro-1,4-benzodioxine-5-carbaldehyde

Product 1

HCID 5343159(E)-3-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)acrylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2,3-dihydrobenzodioxin-5-carboxaldehyde (Morishima, et al., Eur. Pat. Appl. 309,766, 5 Apr. 89) (9.25 g, 56.4 mmol), malonic acid (11.73 g, 112.8 mmol), pyrrolidine (1 mL), and pyridine (25 mL) was heated to reflux for 2 hr, cooled, and then poured into ice water (300 mL). The white precipitate was filtered, washed with 1N HCl, and air dried (9.83 g, 84.6%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hr
  3. temperaturecooled
  4. filtrationThe white precipitate was filtered
  5. washwashed with 1N HCl, and air
  6. customdried (9.83 g, 84.6%)

Sources & evidence

ORD record
ord-3eb3b15e0f8746cdb699671094f732a5
Source dataset
uspto-grants-1999_01
Patent number
US05856529

Linked notes

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