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

HRID 2118213Notes

Reaction equation

HRID 2118213 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]COC)=[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>[OH:28][C:25]1[CH:26]=[CH:27][C:22](/[C:11](/[C:8]2[CH:7]=[CH:6][C:5]([CH:4]=[O:3])=[CH:10][CH:9]=2)=[C:12](\[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)/[CH2:13][CH3:14])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 693166761-[4-(Diethoxymethyl)phenyl]-1-[4-(methoxymethoxy)phenyl]-2-phenylbutan-1-ol

Product 1

HCID 588776594-[(1Z)-1-(4-Hydroxyphenyl)-2-phenylbut-1-enyl]benzaldehydeYield 38.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 16 (194 g, 0.42 mol) in EtOH (1.25 L) was added 12 M HCl (250 mL). The reaction mixture was refluxed for 3 h, cooled to RT, and the volatiles were removed under reduced pressure. H2O (750 mL) was added and the mixture was extracted with ether (3×500 mL). The combined ethereal extracts were washed with H2O (750 mL), brine (750 mL), and dried over MgSO4. Concentration followed by recrystallization from hexanes afforded 52.8 g (38%) of 10 as a white solid. 1HNMR (400 MHz, DMSO-d6): δ 0.83 (t, J=7.3 Hz, 3H), 2.33 (q, J=7.3 Hz, 2H), 6.40 (d, J=8.4 Hz, 2H), 6.60 (d, J=8.4 Hz, 2H), 7.10-7.20 (m, 5H), 7.40 (d, J=7.9 Hz, 2H), 7.90 (d, J=8.1 Hz, 2H), 9.23 (s, 1H), 9.98 (s, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. customthe volatiles were removed under reduced pressure
  3. additionH2O (750 mL) was added
  4. extractionthe mixture was extracted with ether (3×500 mL)
  5. washThe combined ethereal extracts were washed with H2O (750 mL), brine (750 mL)
  6. dry with materialdried over MgSO4
  7. concentrationConcentration
  8. customfollowed by recrystallization from hexanes

Sources & evidence

ORD record
ord-4184695a6df546fe8cc46b4748e7bbcb
Source dataset
uspto-grants-2008_10
Patent number
US07442833B2

Reaction notes

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