Hydrochloric Acid → 4-Cyclohexyl-3-methyl-4-oxo-3-phenylbutanal

HRID 432033Notes

Reaction equation

HRID 432033 reaction equation
C[O:2][CH:3](OC)[CH2:4][C:5]([CH3:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:6]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].Cl>CC(C)=O>[CH:8]1([C:6](=[O:7])[C:5]([CH3:20])([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:4][CH:3]=[O:2])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 120942264-Cyclohexyl-3-methyl-4-oxo-3-phenylbutyraldehyd dimethyl acetal

Product 1

HCID 117801924-Cyclohexyl-3-methyl-4-oxo-3-phenylbutanalYield 97.65%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 82.65 g (66.29 g, 0.2177 mol) of 4-cyclohexyl-3-methyl-4-oxo-3-phenylbutyraldehyde dimethyl acetal in 539 mL of acetone was added 539 mL of 3 N HCl (aq) at RT. After reaction completion (2 h), the mixture was concentrated to 426.5 g (or ⅓ volume) of residue (RT-40° C.). The residue contained mostly water (pH=0) and was extracted twice with 300 mL of MTBE. The MTBE extract was washed with 300 mL of 25% NaCl (aq), dried over MgSO4, gravity filtered and concentrated to afford 54.92 g (97.65%) of title compound as a pink oil: 1H NMR (d6-DMSO): δ9.54 (t, J=2.0 Hz, 1H, —CHO), 7.36-7.45 (m, 2H, phenyl CH), 7.28-7.35 (m, 3H, phenyl CH), 2.95 (dd, J=16.6 Hz, J=1.9 Hz, 1H, CH2CHO), 2.85 (dd, J=16.6 Hz, J=1.7 Hz, 1H, CH2CHO), 2.41-2.49 (m, 1H, cyclohexyl CH), 1.72 (s, 3H, R2C(CH3)Ph), 0.85-1.66 (m, 10H, cyclohexyl —CH2).

Workup

  1. customAfter reaction completion (2 h)
  2. concentrationthe mixture was concentrated to 426.5 g (or ⅓ volume) of residue (RT-40° C.)
  3. extractionwas extracted twice with 300 mL of MTBE
  4. extractionThe MTBE extract
  5. washwas washed with 300 mL of 25% NaCl (aq)
  6. dry with materialdried over MgSO4, gravity
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b5a32dbfe42047769f37ecf6527548f7
Source dataset
uspto-grants-2003_12
Patent number
US06660859B2

Reaction notes

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