Methanol → 2-Methyl-6-phenoxy-benzoic acid methyl ester

HRID 706156Notes

Reaction equation

HRID 706156 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:23]O>>[CH3:23][O:5][C:4](=[O:6])[C:3]1[C:7]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:9]=[CH:10][C:2]=1[CH3:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 671100872-Methyl-6-phenoxy-benzoic acid

Product 1

HCID 671101132-Methyl-6-phenoxy-benzoic acid methyl ester

Procedure

A mixture of 2-methyl-6-phenoxy-benzoic acid (19.9 mmol, 4.54 g), methanol (20 mL), and concentrated sulfuric acid (1.5 mL) was refluxed with stirring for 18 h before it was concentrated in vacuo. To the residue was added water (50 mL) and the mixture was neutralized by adding small portions of NaHCO3 with stirring. Subsequently, the mixture was extracted with ethyl acetate (1×50 mL). The organic phase was dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel using hexanes:ethyl acetate=7:3 as the eluent gave the title compound as a yellowish oil (2.16 g); MS-(+)-ion: M+1=242.8.

Workup

  1. temperaturewas refluxed
  2. concentrationwas concentrated in vacuo
  3. additionTo the residue was added water (50 mL)
  4. additionby adding small portions of NaHCO3
  5. stirringwith stirring
  6. extractionSubsequently, the mixture was extracted with ethyl acetate (1×50 mL)
  7. dry with materialThe organic phase was dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customPurification of the residue by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-ae810900c5f44a88b493abf563cc963b
Source dataset
uspto-grants-2015_11
Patent number
US09174976B2

Reaction notes

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