Sodium Hydroxide → Ethyl 4-hydroxy-3-(2-methylprop-2-en-1-yl)benzoate

HRID 2407472Notes

Reaction equation

HRID 2407472 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([O:11]CC(C)=C)=[CH:7][CH:6]=1)[CH3:2].[OH-].[Na+]>CN1CCCC1=O>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[C:9]([CH2:6][C:5]([CH3:10])=[CH2:4])[CH:10]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 60644252HCID 60644252, compound

Product 1

HCID 18705333Ethyl 4-hydroxy-3-(2-methylprop-2-en-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 4-(2-methylprop-2-enyloxy)benzoic acid ethyl ester (15 g) and 1-methyl-2-pyrrolidinone (150 mL) is heated at reflux for nine hours. The reaction mixture is cooled to room temperature and made basic (pH ˜10) by using aqueous sodium hydroxide solution. The aqueous layer is washed with toluene (2×20 mL) and then made acidic (pH ˜2) with 2N HCl. The aqueous layer is extracted with ethyl acetate (3×20 mL). Combined organic layers are washed with brine (1×15 mL) and dried over sodium sulphate. Removal of solvent gives a dark brown liquid which is purified by column chromatography (silica gel 230-400 mesh, n-hexane:ethyl acetate, 80:20) to give 4-hydroxy-3-(2-methylprop-2-enyl)benzoic acid ethyl ester.

Workup

  1. temperatureis heated
  2. temperatureat reflux for nine hours
  3. washThe aqueous layer is washed with toluene (2×20 mL)
  4. extractionThe aqueous layer is extracted with ethyl acetate (3×20 mL)
  5. washCombined organic layers are washed with brine (1×15 mL)
  6. dry with materialdried over sodium sulphate
  7. customRemoval of solvent
  8. customgives a dark brown liquid which
  9. customis purified by column chromatography (silica gel 230-400 mesh, n-hexane:ethyl acetate, 80:20)

Sources & evidence

ORD record
ord-b3b8c4d82a4041e6af317cc6b3004d18
Source dataset
uspto-grants-2014_08
Patent number
US08809539B2

Reaction notes

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