Hydrochloric Acid → Methyl 3-isobutyl-benzoate

HRID 2421641Notes

Reaction equation

HRID 2421641 reaction equation
CN1[CH2:6][CH2:5][CH2:4][C:3]1=O.[CH2:8]1[CH2:12][O:11][CH2:10][CH2:9]1.[CH2:13]([Mg]Br)[CH:14]([CH3:16])[CH3:15].Cl.[OH2:20]>>[CH3:10][O:11][C:12](=[O:20])[C:8]1[CH:9]=[CH:6][CH:5]=[C:4]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH:3]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 13387N-methyl-2-pyrrolidoneHCID 178418816HCID 178418816, compound

Product 1

HCID 20771995Methyl 3-isobutyl-benzoate

Procedure

Compound from example 76A (1.62 g, 6 mmol), N-methylpyrrolidinone (3.4 mL), Fe(acac)3 (140 mg, 0.4 mmol) and dry THF (35 mL) were stirred under nitrogen at room temperature. Isobutylmagnesium bromide (2.0 M in Et2O, 3.6 mL) was added by syringe. After stirring for fifteen minutes, HCl (2 M, 20 mL) was slowly added. The mixture was diluted with water and extracted three times with EtOAc. The organic layers were combined, washed with water and then brine, were dried over MgSO4 and were concentrated. Purification was achieved using flash chromatography on SiO2 with hexanes/toluene 75:25. A colourless oil was obtained (1.07 g, 93%). NMR 1H (ppm, CDCl3): 7.94-7.89 (m, 2H), 7.39-7.33 (m, 2H), 3.89 (s, 3H), 2.51 (d, J3=7.2 Hz, 2H), 1.94-1.85 (m, 1H), 0.89 (t, J3=6.6 Hz, 6H).

Workup

  1. extractionextracted three times with EtOAc
  2. washwashed with water
  3. dry with materialbrine, were dried over MgSO4
  4. concentrationwere concentrated
  5. customPurification
  6. customA colourless oil was obtained (1.07 g, 93%)

Sources & evidence

ORD record
ord-dd882f2029e34ca9ad887c9bc6e9aac8
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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