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

HRID 1107554Notes

Reaction equation

HRID 1107554 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, Apr. 5, 1989) (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-04cf1a436de6409ca69f7fb1cfa8a35d
Source dataset
uspto-grants-2000_05
Patent number
US06060506

Reaction notes

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