1-Methyl-1,4-cyclohexadiene → 4-Hydroxy-2-isopropoxybenzaldehyde

HRID 1805918Notes

Reaction equation

HRID 1805918 reaction equation
C([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([O:17][CH:18]([CH3:20])[CH3:19])[CH:10]=1)C1C=CC=CC=1.CC1CC=CCC=1>[Pd]>[OH:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([O:17][CH:18]([CH3:20])[CH3:19])[CH:10]=1

Participants

4

Reactant 2

HCID 780061-Methyl-1,4-cyclohexadieneHCID 106357444-(Benzyloxy)-2-isopropoxybenzaldehyde

Product 1

HCID 722219574-Hydroxy-2-isopropoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A suspension of 10% palladium on carbon (0.793 g, 0.745 mmol) in a solution of 4-(benzyloxy)-2-isopropoxybenzaldehyde (4.03 g, 14.91 mmol) and 1-methyl-1,4-cyclohexadiene (16.75 mL, 149 mmol) in DOH (298 mL) was heated at reflux for 2 h. The reaction mixture was cooled to room temperature, filtered through a plug of Celite and washed through with EtOAc. The filtrate was concentrated in vacuo to afford 4-hydroxy-2-isopropoxybenzaldehyde, as a colorless solid. LCMS calc.=181.1; found=181.0 (M+H)+. 1H NMR (500 MHz, CHCl3): δ 10.12 (s, 1H); 7.74 (d, J=8.6 Hz, 1 H); 6.52 (dd, J=8.7, 2.1 Hz, 1 H); 6.47 (d, J=2.1 Hz, 1 H); 4.62-4.54 (m, 1 H); 1.36 (d, J=6.1 Hz, 6 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. filtrationfiltered through a plug of Celite
  4. washwashed through with EtOAc
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-996c4ef7b09e478fa5a6edf643fdfcd5
Source dataset
uspto-grants-2013_01
Patent number
US08354454B2

Reaction notes

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