Methanol → HCID 18324374, compound

HRID 1251903Notes

Reaction equation

HRID 1251903 reaction equation
S(Cl)(Cl)(=O)=O.[OH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:8]=1.[CH3:23]O>>[CH3:15][CH2:7][CH2:8][CH:9]([CH3:16])[CH3:10].[OH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([O:13][CH3:23])=[O:12])=[C:9]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24648Sulfuryl chlorideHCID 23499550HCID 23499550, compound

Product 2

HCID 78922-MethylpentaneHCID 18324374HCID 18324374, compoundYield 65%

Procedure

Sulphuryl chloride (4.4 ml) was carefully added to a solution of 4-hydroxy-2-(4-fluorophenyl)benzoic acid (20.8 g, 0.0896 mol) (from Example 32) in methanol (220 ml) and the mixture heated at reflux for 16 hours. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and aqueous NaHCO3 (pH ˜8). The organic phase was washed with water, brine, dried (MgSO4), filtered and evaporated to give a sticky brown solid which, on trituration with isohexane, gave methyl 4-hydroxy-2-(4-fluorophenyl)benzoate (14.34 g, 65% yield).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 16 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe residue partitioned between ethyl acetate and aqueous NaHCO3 (pH ˜8)
  5. washThe organic phase was washed with water, brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customto give a sticky brown solid which

Sources & evidence

ORD record
ord-f91c06903a174c3b8defd61d54b0564a
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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