Methanol → HCID 20304315, compound

HRID 1732643Notes

Reaction equation

HRID 1732643 reaction equation
C([O:4][CH2:5][C:6]1[C:7]([F:19])=[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:9]=[CH:10][C:11]=1[F:12])(=O)C.[OH-].[Na+].CO>C(O)(=O)C>[F:19][C:7]1[C:6]([CH2:5][OH:4])=[C:11]([F:12])[CH:10]=[CH:9][C:8]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 20304304HCID 20304304, compound

Product 1

HCID 20304315HCID 20304315, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3.1 g (0.012 mole) of (2,4-difluoro[1,1'-biphenyl]-3-yl)methyl acetate in 25 ml of a 2% aqueous solution of sodium hydroxide and 75 ml of methanol was stirred at ambient temperature until the reaction was complete as indicated by thin layer chromatography. The reaction mixture was neutralized with glacial acetic acid and concentrated under reduced pressure to give a residual solid. The solid was partitioned between diethyl ether and water. The phases were separated and the aqueous phase was extracted with two portions of diethyl ether. The ether layers were combined and washed with one portion of 150 ml of 2% aqueous hydrochloric acid, one portion of 150 ml of water, one portion of 150 ml of a 10% aqueous solution of sodium carbonate, one portion of 150 ml of water, and finally, one portion of a saturated aqueous solution of sodium chloride. The organic layer was dried with magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to give 2.3 g of 2,4-difluoro[1,1'-biphenyl]-3-methanol. The nmr spectrum was consistent with the proposed structure.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto give a residual solid
  3. customThe solid was partitioned between diethyl ether and water
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with two portions of diethyl ether
  6. washwashed with one portion of 150 ml of 2% aqueous hydrochloric acid, one portion of 150 ml of water, one portion of 150 ml of a 10% aqueous solution of sodium carbonate, one portion of 150 ml of water
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-8d1295a4e52b4b0d8fa7987bb92406e6
Source dataset
uspto-grants-1980_12
Patent number
US04238505

Reaction notes

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