Methanol → Methyl 2-(4-methylphenoxy)benzoate

HRID 653911Notes

Reaction equation

HRID 653911 reaction equation
[CH3:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:23]O>>[CH3:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([O:11][CH3:23])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 5786562-(4-Methylphenoxy)benzoic acid

Product 1

HCID 618012Methyl 2-(4-methylphenoxy)benzoate

Procedure

A solution of 37.70 g of 2-(4-methylphenoxy)-benzoic acid was 12.0 mL of concentrated sulfuric acid in 500 mL of methanol was refluxed for 14 hours. After cooling, the reaction mixture was concentrated in vacuo and the residue was added to a mixture of methylene chloride and water. The organic phase was separated, washed with saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was kugelrohr distilled (120°-135°/0.025 torr) to furnish 35.08 g of methyl 2-(4-methylphenoxyl)benzoate, m.p. 31°-34°. NMR (200 MHz, CDCl3) δ 7.87 (d of d, 1H); 7.39 (t of d, 1H); 7.11 (m, 3H); 6.88 (m, 3H); 3.81 (s, 3H); 2.30 (s, 3H).

Workup

  1. temperaturewas refluxed for 14 hours
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. additionthe residue was added to a mixture of methylene chloride and water
  5. customThe organic phase was separated
  6. washwashed with saturated sodium bicarbonate solution and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. distillationThe crude product was kugelrohr distilled (120°-135°/0.025 torr)

Sources & evidence

ORD record
ord-29175f96a9554ac4b9b1c8a817d74eb4
Source dataset
uspto-grants-1992_07
Patent number
US05128355

Reaction notes

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