Methyl 4-Formylbenzoate → Benzoic acid, 4-(1-hydroxypropyl)-, methyl ester

HRID 1914261Notes

Reaction equation

HRID 1914261 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][CH:5]=1.[CH2:13]([Mg]Br)[CH3:14]>C1COCC1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:11])[CH2:13][CH3:14])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 15294Methyl 4-FormylbenzoateHCID 178418443HCID 178418443, compound

Product 1

HCID 12105276Benzoic acid, 4-(1-hydroxypropyl)-, methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-formyl-benzoic acid methyl ester (3.0 g, 18.3 mmol) in THF (10 mL) at 0° C. is added ethylmagnesium bromide (2M, 10 mL). After stirring at room temperature for 2 hours, it is quenched with saturated ammonium chloride, extracted with EtOAc. The organic is concentrated to give the titled compound as colorless oil: 2.2 g (62%).

Workup

  1. customit is quenched with saturated ammonium chloride
  2. extractionextracted with EtOAc
  3. concentrationThe organic is concentrated

Sources & evidence

ORD record
ord-becc85dda06d4372a10918f50cb27241
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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