Formaldehyde → HCID 44631777, compound

HRID 280293Notes

Reaction equation

HRID 280293 reaction equation
C(NCC)C.[CH2:6]([O:8][C:9](=[O:22])[CH:10]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=1)[C:11](O)=O)[CH3:7].C=O>O>[Cl:21][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[CH2:14][C:10](=[CH2:11])[C:9]([O:8][CH2:6][CH3:7])=[O:22]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8021DiethylamineHCID 54419678HCID 54419678, compound

Product 1

HCID 44631777HCID 44631777, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diethylamine (27.6 g, 39 ml) is added dropwise with shaking to 3-chlorobenzylmalonic acid monoethyl ester (90.0 g) [Chem. Ber. 92, 203 (1959)], in a flask cooled in a water bath. Aqueous formaldehyde (37%, 38 ml) is added dropwise with shaking and cooling as before. Gas is evolved, and the reaction mixture becomes lighter in color. The mixture is stirred at room temperature for 65 hours, then water (500 ml) is added, and the solution extracted with ether (2×350 ml). The combined ether solutions are washed with water (300 ml), 3N HCl (2×200 ml) and water (300 ml). The ether solution is dried over magnesium sulfate, and the solvent removed under reduced pressure to give ethyl α-(3-chlorobenzyl)acrylate as a yellow oil, NMR (CDCl3)δ: 7.15 (m, 4H), 6.22 (s, 1H), 5.45 (m, 1H), 4.13 (q, 2H), 3.58 (s, 2H), 1.23 (t, 3H).

Workup

  1. temperaturecooled in a water bath
  2. temperaturecooling as before
  3. stirringThe mixture is stirred at room temperature for 65 hours
  4. extractionthe solution extracted with ether (2×350 ml)
  5. washThe combined ether solutions are washed with water (300 ml), 3N HCl (2×200 ml) and water (300 ml)
  6. dry with materialThe ether solution is dried over magnesium sulfate
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-067832bba7894cdeb179adc65c081305
Source dataset
uspto-grants-1986_05
Patent number
US04588746

Reaction notes

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