Hydrochloric Acid → HCID 20463693, compound

HRID 326006Notes

Reaction equation

HRID 326006 reaction equation
CN(C)C.[CH2:5]([O:7][C:8](=[O:14])[CH2:9][C:10]([CH2:12]Cl)=O)[CH3:6].Cl>>[CH2:5]([O:7][C:8]([C:9]1[CH2:12][CH:10]=[C:9]([C:8]([O:7][CH2:5][CH3:6])=[O:14])[CH2:12][CH:10]=1)=[O:14])[CH3:6]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 1146TrimethylamineHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 20463693HCID 20463693, compound

Conditions

Temperature
10 °C

Procedure

In a 2.5 liter double casing vessel, equipped with a discharge cock, a mechanical stirrer and thermometer, 1062.7 g of trimethylamine (44.5 percent in water=472.9 g, 100 percent=8 mole) was put up and cooled to 10° C. By means of a dosing pump and a hose submerged in the TMA solution, 272.8 g of 4-chloroacetoacetic acid ethyl ester (96.0 percent=261.9 g, 100 percent=1.59 mole) was added by doses during 3 hours at 10° to 12° C. and the yellowish reaction mixture was concentrated at 40° C. and 25 torr in such manner until the pH value reached 7.6. The excess TMA was subsequently condensed out by means of three cooling traps and was recaptured. After a slight lowering of the pH value with 65 ml of 36% hydrochloric acid to 6 and after the filtering out of the yellowish precipitate obtained (2,5-diethoxycarbonyl-1,4-cyclohexadiene), the reaction solution was hydrogenated in a 2-liter autoclave equipped with a stirring mechanism for 7 hours at 10° C. and 11 atu of pressure with the help of 8.8 g of platinum/activated charcoal catalyst.

Workup

  1. customIn a 2.5 liter double casing vessel, equipped with a discharge cock, a mechanical stirrer
  2. additionwas added by doses during 3 hours at 10° to 12° C.
  3. customthe yellowish reaction mixture
  4. concentrationwas concentrated at 40° C.
  5. customcondensed out by means of three cooling traps

Sources & evidence

ORD record
ord-31a6966583d248f094ca9be6dae2c5e1
Source dataset
uspto-grants-1984_04
Patent number
US04443627

Reaction notes

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