Ammonium Chloride → Methyl 4-(1-hydroxyethyl)-3-methoxybenzoate

HRID 1909866Notes

Reaction equation

HRID 1909866 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:13][CH3:14])=[O:2].[CH3:15][Mg]Br.[Cl-].[NH4+]>C1COCC1>[OH:2][CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:13][CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10631650Methyl 4-formyl-3-methoxybenzoateHCID 178418573HCID 178418573, compound

Product 1

HCID 58306433Methyl 4-(1-hydroxyethyl)-3-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 4-formyl-3-methoxybenzoate (3.30 g) and THF (30 mL) was added dropwise methyl magnesium bromide (3 M diethyl ether solution, 3.60 mL) under ice-cooling. After dropwise addition, the mixture was stirred for 1 hour under ice-cooling. A saturated aqueous ammonium chloride solution was added thereto to stop the reaction, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, and then dried over an aqueous anhydrous sodium sulfate solution. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain methyl 4-(1-hydroxyethyl)-3-methoxybenzoate (1.92 g).

Workup

  1. temperaturecooling
  2. additionAfter dropwise addition
  3. temperaturecooling
  4. customthe reaction
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over an aqueous anhydrous sodium sulfate solution
  8. customThe solvent was evaporated under reduced pressure
  9. customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-05e723b7b19f4cb7b3d68f5d5abc2378
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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