Methanol → Methyl 2-(4-fluorophenethyl)-5-hydroxybenzoate

HRID 1251893Notes

Reaction equation

HRID 1251893 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][CH2:7][C:8]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.S(Cl)(Cl)(=O)=O.[CH3:25]O>>[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][CH2:7][C:8]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:9]=2[C:10]([O:12][CH3:25])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24648Sulfuryl chlorideHCID 183245242-(4-Fluorophenethyl)-5-hydroxybenzoic acid

Product 1

HCID 18324453Methyl 2-(4-fluorophenethyl)-5-hydroxybenzoateYield 66%

Procedure

A solution of 2-(4-fluorophenethyl)-5-hydroxybenzoic acid (30 g, 115.4 mmol) in methanol (900 ml) and the stirred solution treated dropwise with sulphuryl chloride (1.6 ml, 19.6 mmol) stirred and heated at reflux for 16 hours. The mixture was evaporated to dryness, the residue dissolved in ethyl acetate (500 ml), washed with saturated aqueous NaHCO3 (×2), water and brine. After drying (MgSO4) the solution was evaporated to dryness to give a brown oil which when triturated with iso-hexane gave methyl 2-(4-fluorophenethyl)-5-hydroxybenzoate (21.02 g, 66%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 hours
  3. customThe mixture was evaporated to dryness
  4. dissolutionthe residue dissolved in ethyl acetate (500 ml)
  5. washwashed with saturated aqueous NaHCO3 (×2), water and brine
  6. dry with materialAfter drying (MgSO4) the solution
  7. customwas evaporated to dryness
  8. customto give a brown oil which when
  9. customtriturated with iso-hexane

Sources & evidence

ORD record
ord-692ad3dbf6c44f01aaa0d7a9ccecb47d
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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