Hydrochloric Acid → 4-[1-(4-Methoxyphenyl)-2-phenylbut-1-enyl]benzaldehyde

HRID 2118203Notes

Reaction equation

HRID 2118203 reaction equation
C([O:3][CH:4](OCC)[C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)(O)[CH:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][CH3:14])=[CH:7][CH:6]=1)C.Cl>CCO>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([C:11]([C:8]2[CH:9]=[CH:10][C:5]([CH:4]=[O:3])=[CH:6][CH:7]=2)=[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][CH3:14])=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 588776601-[4-(Diethoxymethyl)phenyl]-1-(4-methoxyphenyl)-2-phenylbutan-1-ol

Product 1

HCID 724505544-[1-(4-Methoxyphenyl)-2-phenylbut-1-enyl]benzaldehyde

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of compound 3 (163.09 g, 375 mmol) in EtOH (750 mL) was charged with concentrated aqueous HCl (150 mL) and the resulting solution heated at 80° C. for 90 min. The solution was allowed to cool to RT and then was concentrated to the aqueous layer. H2O (500 mL) was added and the mixture extracted with CH2Cl2 (3×150 mL). The combined organic layers were dried (MgSO4) and concentrated to provide 4 (119.78 g, 93% over 2 steps) as a brown oil (3:1 mixture of Z:E isomers). The mixture was carried on without further purification. Z-isomer: 1H NMR (400 MHz, CDCl3): δ 0.94 (t, J=7.5 Hz, 3H), 2.45 (q, J=7.5 Hz, 2H), 3.68 (s, 3H), 6.56 (d, J=8.6 Hz, 2H), 6.75 (d, J=8.6 Hz, 2H), 7.08-7.21 (m, 5H), 7.41 (d, J=8.1 Hz, 2H), 7.87 (d, J=8.1 Hz, 2H), 10.02 (s, 1H). E-isomer: 1H NMR (CDCl3): δ 0.97 (t, J=7.4 Hz, 3H), 2.52 (q, 7.4 Hz, 2H), 3.83 (s, 3H), 6.90 (d, J=8.3 Hz, 2H), 7.03 (d, J=8.3 Hz, 2H), 7.0-8-7.21 (m, 7H), 7.51 (d, J=8.1 Hz, 2H), 9.83 (s, 1H).

Workup

  1. temperatureto cool to RT
  2. concentrationwas concentrated to the aqueous layer
  3. additionH2O (500 mL) was added
  4. extractionthe mixture extracted with CH2Cl2 (3×150 mL)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated
  7. customto provide 4 (119.78 g, 93% over 2 steps)
  8. additionas a brown oil (3:1 mixture of Z:E isomers)
  9. customThe mixture was carried on without further purification

Sources & evidence

ORD record
ord-2979f992801f4d08861f05b7b7bbea2b
Source dataset
uspto-grants-2008_10
Patent number
US07442833B2

Reaction notes

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