Methyl 4-Formylbenzoate → Methyl 4-(1-hydroxy-3-methylbutyl)benzoate

HRID 658303Notes

Reaction equation

HRID 658303 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)[CH:14]([CH3:16])[CH3:15]>C1COCC1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:11])[CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 15294Methyl 4-FormylbenzoateHCID 178418816HCID 178418816, compound

Product 1

HCID 59518172Methyl 4-(1-hydroxy-3-methylbutyl)benzoateYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-formyl-benzoic acid methyl ester (32.4 g, 147 mmol) in anhydrous THF (800 mL) is cooled to 0° C. while stirring under nitrogen. Isobutyl magnesium bromide (2.0M in diethyl ether, 110 mL, 221 mmol) is added slowly over 10 min. The reaction is allowed to stir at 0° C. for 1 h, and then allowed to warm to room temperature. The reaction is monitored by HPLC, and upon complete consumption of the aldehyde, the reaction is quenched carefully with 1N HCl. The reaction is diluted with diethyl ether and water, followed by extraction. The organic layer is washed with water and brine, followed by drying over anhydrous sodium sulfate. The solution is filtered and concentrated, then further purified using flash column chromatography using ethyl acetate/hexanes to provide 12 g (37%) of product.

Workup

  1. stirringto stir at 0° C. for 1 h
  2. customupon complete consumption of the aldehyde
  3. customthe reaction is quenched carefully with 1N HCl
  4. additionThe reaction is diluted with diethyl ether and water
  5. extractionfollowed by extraction
  6. washThe organic layer is washed with water and brine
  7. dry with materialby drying over anhydrous sodium sulfate
  8. filtrationThe solution is filtered
  9. concentrationconcentrated
  10. customfurther purified

Sources & evidence

ORD record
ord-c1c8199738b04f509344cda937a62e17
Source dataset
uspto-grants-2011_12
Patent number
US08076374B2

Reaction notes

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