4-(3-Methylbutanoyl)benzoic acid → Tert-butyl 4-(3-methylbutanoyl)benzoate

HRID 1424284Notes

Reaction equation

HRID 1424284 reaction equation
[CH3:1][CH:2]([CH3:15])[CH2:3][C:4]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)=[O:5]>ClCCl.COC(C)(C)C>[CH3:1][CH:2]([CH3:15])[CH2:3][C:4]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:12][C:2]([CH3:15])([CH3:3])[CH3:1])=[O:11])=[CH:8][CH:7]=1)=[O:5]

Participants

4

Reactant 1

HCID 681567904-(3-Methylbutanoyl)benzoic acid

Product 1

HCID 71239698Tert-butyl 4-(3-methylbutanoyl)benzoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a slurry of 4-(3-methylbutanoyl)benzoic acid (499 mg, 2.42 mmol) in dichloromethane (6 mL) was added O-tert-butyl-NN-diisopropylisourea (1.82 g, 9.07 mmol). The mixture was stirred at room temperature for 50 hours then diluted with tert-butyl methyl ether (75 mL). The mixture was washed with sat. aq sodium bicarbonate (50 mL), dried over anhydrous Na2SO4, and filtered, and the filtrate was concentrated. Purification by silica gel flash chromatography (ethyl acetate/heptane) gave tert-butyl 4-(3-methylbutanoyl)benzoate as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 8.09-8.04 (m, 2H), 8.00-7.94 (m, 2H), 2.86 (d, J=6.8 Hz, 2H), 2.37-2.23 (m, 1H), 1.62 (s, 9H), 1.01 (d, J=6.7 Hz, 6H).

Workup

  1. washThe mixture was washed with sat. aq sodium bicarbonate (50 mL)
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customPurification by silica gel flash chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-a5d9d14d20ef43e7993dbf42061969eb
Source dataset
uspto-grants-2015_01
Patent number
US08927577B2

Reaction notes

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