Hydrochloric Acid → HCID 21569134, compound

HRID 1579832Notes

Reaction equation

HRID 1579832 reaction equation
[Cl:1][CH:2]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=2)[CH:9]=1)[C:3]([O:5]CC)=[O:4].Cl>C(O)(=O)C>[Cl:1][CH:2]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=2)[CH:9]=1)[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21569131HCID 21569131, compound

Product 1

HCID 21569134HCID 21569134, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.167 moles of the ethyl α-chloro-6-methoxy-2-naphthylacetate and 160 ml. of glacial acetic acid containing 40 ml. of 37% hydrochloric acid is refluxed for 20 hours. The mixture is concentrated under reduced pressure to give a gummy residue. The latter material is dissolved in 300 ml. of n-hexane, washed with ice-cold water (100 ml. total), dried over sodium sulfate and filtered. The hexane is removed to give α-chloro-6-methoxy-2-naphthylacetic acid.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. customto give a gummy residue
  3. dissolutionThe latter material is dissolved in 300 ml
  4. washof n-hexane, washed with ice-cold water (100 ml. total)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customThe hexane is removed

Sources & evidence

ORD record
ord-62d84acf7e044341bb3a3e1bb4768443
Source dataset
uspto-grants-1976_01
Patent number
US03931269

Reaction notes

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