Ethyl 4-chloroacetoacetate → HCID 14372562, compound

HRID 1702578Notes

Reaction equation

HRID 1702578 reaction equation
[Cl:1][CH2:2][C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH:11]([O-])([O-])OC>>[CH3:11][O:10]/[C:3](/[CH2:2][Cl:1])=[CH:4]\[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

3

Reactant 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 53629101Methylorthoformate

Product 1

HCID 14372562HCID 14372562, compoundYield 83%

Procedure

Two grams of amberlyst 15 ion exchange resin was added to a solution of 8.23 g (0.05 mol) of ethyl 4-chloroacetoacetate in 25 mL of methyl orthoformate. The solution was stirred overnight, the resin was filtered, and excess ortho ester was removed in vacuo. The residue was then heated slowly over 1 h to 190° C., after which it was allowed to cool and then short path distilled to yield 7.37 g (83%) of ethyl 3-methoxy-4-chlorocrotonate as a colorless liquid: bp 145°-148° C. (40 mm); VPC (6 ft 5% SF 96 on 60-80 mesh chromosorb G; 160° C.; 60 cm3 /min He flow) tR =1.9 min; NMR (CDCl3) 1.10 (t, 3H, J=7 Hz, COOCCH3), 3.73(s, 3H, OCH3), 4.20 (q, COOCH2C, J=7 Hz, COOCH2C), 4.67 (s, 2H, ClCH2), 5.17 (s, 1H, CH).

Workup

  1. filtrationthe resin was filtered
  2. customexcess ortho ester was removed in vacuo
  3. temperatureThe residue was then heated slowly over 1 h to 190° C.
  4. temperatureto cool
  5. distillationshort path distilled

Sources & evidence

ORD record
ord-6469ce9cf0d74e61babd5ca003f05b83
Source dataset
uspto-grants-1982_09
Patent number
US04348333

Reaction notes

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