Methanol → Methyl 3-(3-hydroxyphenyl)-5-hexenoate

HRID 1662355Notes

Reaction equation

HRID 1662355 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]([CH2:13][CH:14]=[CH2:15])[CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=1.[CH3:16]O>S(=O)(=O)(O)O.CCOC(C)=O>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]([CH2:13][CH:14]=[CH2:15])[CH2:9][C:10]([O:12][CH3:16])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 577065823-(3-Hydroxyphenyl)-5-hexenoic acid

Product 1

HCID 57707209Methyl 3-(3-hydroxyphenyl)-5-hexenoateYield 84%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 43.2 (2.4 g, 12 mmol) in MeOH (25 mL) was added five drops of sulfuric acid. The mixture was stirred overnight at reflux, cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (MgSO4), and concentrated. The crude product was chromatographed on silica gel (0-25% EtOAc/hexane) to afford 43.3 (2.2 g, 84%) as a colorless oil.

Workup

  1. temperatureat reflux
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude product was chromatographed on silica gel (0-25% EtOAc/hexane)

Sources & evidence

ORD record
ord-32e962bfd3e94c4ea232c1380ccabc8e
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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