Methanol → 4-(4-Fluorophenethyl)-3-methoxycarbonylbenzoic acid

HRID 1251868Notes

Reaction equation

HRID 1251868 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][CH2:7][C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][C:9]=2[C:18]([O:20][CH3:21])=[O:19])=[CH:4][CH:3]=1.O1CCOCC1.CO.[OH-].[Na+]>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][C:8]2[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=2[C:18]([O:20][CH3:21])=[O:19])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 18474597Methyl 4-(4-fluorophenethyl)-3-methoxycarbonylbenzoate

Product 1

HCID 184746364-(4-Fluorophenethyl)-3-methoxycarbonylbenzoic acidYield 86.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 4-(4-fluorophenethyl)-3-methoxycarbonylbenzoate (51.00 g., 161.22 mmol), dioxane (650 ml), methanol (650 ml), sodium hydroxide (7.10 g., 177.35 mmol) and water (100 ml) was stirred at ambient temperature under an inert atmosphere for 16 hours. The reaction was evaporated to dryness, water (500 ml) added to the residue and the mixture extracted with diethylether. The organic extracts were dried and evaporated to dryness to give recovered methyl 4-(4-fluorophenethyl)-3-methoxycarbonylbenzoate (7 g). The aqueous layer was acidified to pH 2 with 2M HCl (300 ml) and extracted with ethyl acetate (300 ml). The organic extracts were dried, filtered and evaporated to dryness to give, as a white solid, 4-(4-fluorophenethyl)-3-methoxycarbonylbenzoic acid (42.00 g).

Workup

  1. customThe reaction was evaporated to dryness, water (500 ml)
  2. additionadded to the residue
  3. extractionthe mixture extracted with diethylether
  4. customThe organic extracts were dried
  5. customevaporated to dryness
  6. customto give
  7. customrecovered methyl 4-(4-fluorophenethyl)-3-methoxycarbonylbenzoate (7 g)
  8. extractionextracted with ethyl acetate (300 ml)
  9. customThe organic extracts were dried
  10. filtrationfiltered
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-0536b84a67b84580aac955a4d845a0e7
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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