2-Isobutylsuccinic acid-4-t-butyl ester-1-methyl ester → 2-Isobutyl-succinic acid-4-t-butyl ester

HRID 458069Notes

Reaction equation

HRID 458069 reaction equation
C[O:2][C:3](=[O:17])[CH:4]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]>Cl.CC(C)=O>[C:9]([O:8][C:6](=[O:7])[CH2:5][CH:4]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:3]([OH:17])=[O:2])([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 1

HCID 218883142-Isobutylsuccinic acid-4-t-butyl ester-1-methyl ester

Product 1

HCID 99427122-Isobutyl-succinic acid-4-t-butyl esterYield 97%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

Acetal 2 (1.01 g, 5.54 mmol) was stirred in a mixture of 2N hydrochloric acid (10 mL) and acetone (10 mL) for 24 hours. After this time, tlc showed complete consumption of the starting acetal. Saturated sodium carbonate solution (20 mL) was added, and the mixture was extracted with ether (3×25 mL). The combined ether fractions were washed with brine, dried (MgSO4), and the solvent was evaporated under reduced pressure. The residue was chromatographed (SiO2, pentane/ether, 95:5) to give the ketone 3 (0.75 g, 97%) as a colorless oil; Rf (heptane/ethyl acetate, 8:2) 0.42; νmax(film)/cm−1 1743 (C═O); δH (400 MHz; CDCl3): 2.37–2.28 (2H, m), 2.20 (2H, dd, J=18.5, 7.5), 2.12 (2H, dd, J=18.7, 6.3), 1.65–1.24 (10H, m).

Workup

  1. customconsumption of the starting acetal
  2. additionSaturated sodium carbonate solution (20 mL) was added
  3. extractionthe mixture was extracted with ether (3×25 mL)
  4. washThe combined ether fractions were washed with brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was chromatographed (SiO2, pentane/ether, 95:5)

Sources & evidence

ORD record
ord-8c4facf2811e46468eb273e5026a3a87
Source dataset
uspto-grants-2007_03
Patent number
US07189747B2

Reaction notes

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