Methanol → HCID 54182122, compound

HRID 972360Notes

Reaction equation

HRID 972360 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19].[CH3:20]O>S(=O)(=O)(O)O>[F:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]([O:11][CH3:20])=[O:10])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19]

Participants

4

Reactant 2

HCID 887MethanolHCID 21406751HCID 21406751, compound

Product 1

HCID 54182122HCID 54182122, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2,2',4'-trifluoro-4-biphenylyl acetic acid (10 g.) in anhydrous methanol (100 ml.) and concentrated sulphuric acid (5 ml.) was refluxed overnight. Excess solvent was distilled and the residue was poured onto ice-water and extracted with ether. The extracts were washed with dilute aqueous sodium bicarbonate and then dried, evaporated and distilled to give a yellow oil, b.p. 142°-146°/0.5 mm., which solidified on cooling. This was crystallized from 62-68 petroleum ether to give methyl 2,2',4'-trifluoro-4-biphenylylacetate, m.p. 74°-77° C.

Workup

  1. distillationExcess solvent was distilled
  2. additionthe residue was poured onto ice-water
  3. extractionextracted with ether
  4. washThe extracts were washed with dilute aqueous sodium bicarbonate
  5. customdried
  6. customevaporated
  7. distillationdistilled
  8. customto give a yellow oil, b.p. 142°-146°/0.5 mm
  9. temperatureon cooling
  10. customThis was crystallized from 62-68 petroleum ether

Sources & evidence

ORD record
ord-22ea3e4e51eb4f7ba8f773ba3f78b091
Source dataset
uspto-grants-1977_10
Patent number
US04052514

Reaction notes

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