Hydrochloric Acid → Fenclorac

HRID 436316Notes

Reaction equation

HRID 436316 reaction equation
[Cl:1][CH:2]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:10]([Cl:20])[CH:9]=1)[C:3]([O:5]CC)=[O:4].Cl>C(O)(=O)C>[Cl:1][CH:2]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)=[C:10]([Cl:20])[CH:9]=1)[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21454144Ethyl alpha,3-dichloro-4-cyclohexylphenylacetate

Product 1

HCID 37494Fenclorac

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 52.5 g. (0.167 moles) of the ethyl α,3-dichloro-4-cyclohexylphenylacetate 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,3-dichloro-4-cyclohexylphenylacetic acid.

Workup

  1. additionA mixture of 52.5 g
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customto give a gummy residue
  4. dissolutionThe latter material is dissolved in 300 ml
  5. washof n-hexane, washed with ice-cold water (100 ml. total)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customThe hexane is removed

Sources & evidence

ORD record
ord-7cadc034728d42bf89c03b0c47f8e72a
Source dataset
uspto-grants-1977_02
Patent number
US04008269

Reaction notes

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