Thionyl Chloride → HCID 21569131, compound

HRID 1579831Notes

Reaction equation

HRID 1579831 reaction equation
[Cl:1][C:2]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[CH:10]=1)(O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].S(Cl)(Cl)=O>>[Cl:1][CH:2]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 21569139HCID 21569139, compound

Product 1

HCID 21569131HCID 21569131, compound

Procedure

A mixture of 0.747 mole of ethyl α-chloro-6-methoxy-2-naphthylglycolate is stirred with 106.67 g. (0.895 mole) of thionyl chloride at room temperature for 24 hours and then heated to reflux for 6 hours. The cold reaction mixture is poured into 1125 ml. of ice-cold water with stirring. The mixture is extracted with 800 ml. of ether. The ethereal solution is washed with 450 ml. of cold saturated sodium hydrocarbonate solution followed by washing twice, each time with 250 ml. of cold water. The ethereal solution is dried over anhydrous sodium sulfate and filtered. The solvent is removed in vacuo to obtain ethyl α-chloro-6-methoxy-2-naphthylacetate.

Workup

  1. temperatureheated
  2. temperatureto reflux for 6 hours
  3. customThe cold reaction mixture
  4. additionis poured into 1125 ml
  5. stirringof ice-cold water with stirring
  6. extractionThe mixture is extracted with 800 ml
  7. washThe ethereal solution is washed with 450 ml
  8. washby washing twice
  9. dry with materialThe ethereal solution is dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-99de6f2a91aa4697a7cfa8078f4e657e
Source dataset
uspto-grants-1976_01
Patent number
US03931269

Reaction notes

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