HCID 23053723, compound → HCID 23053728, compound

HRID 1650167Notes

Reaction equation

HRID 1650167 reaction equation
[Cl:1][C:2](=[CH2:15])[CH2:3][C:4]1[C:5]([OH:14])=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8].Cl[C:17](=C)COC1C=CC=CC=1C(OC)=O>>[Cl:1][C:2](=[CH2:15])[CH2:3][C:4]1[C:5]([OH:14])=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH2:10][CH3:17])=[O:8]

Participants

3

Reactant 2

HCID 23053723HCID 23053723, compoundHCID 23053735HCID 23053735, compound

Product 1

HCID 23053728HCID 23053728, compoundYield 88%

Conditions

Temperature
260 °C

Procedure

Methyl 3-(2-chloro-2-propenyl)-2-hydroxybenzoate. 274.1 g (1.21 mole) of methyl 2-(2-chloro-2-propenyloxy)-benzoate, placed in a 2 liter round-bottomed flask, are carefully degassed with argon. This is then heated as rapidly as possible to 260° C. At this temperature, an exothermic reaction takes place suddenly: the temperature increases to 293° C. by itself and reflux and blackening of the reaction mixture takes place. After cooling to ambient temperature, the product is distilled under reduced pressure. 241.1 g of ethyl 3-(2-chloro-2-propenyl)-2-hydroxybenzoate are obtained.

Workup

  1. customare carefully degassed with argon
  2. customAt this temperature, an exothermic reaction
  3. temperaturethe temperature increases to 293° C. by itself
  4. temperaturereflux
  5. temperatureAfter cooling to ambient temperature
  6. distillationthe product is distilled under reduced pressure

Sources & evidence

ORD record
ord-25c663889f0346bb9067b7c59e93d2dc
Source dataset
uspto-grants-1990_05
Patent number
US04923865

Reaction notes

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