Hydrochloric Acid → 5-Methoxy-2-methylphenol

HRID 2307880Notes

Reaction equation

HRID 2307880 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.Cl>C(OCC)(=O)C.[Pd]>[CH3:11][O:10][C:8]1[CH:7]=[CH:6][C:3]([CH3:4])=[C:2]([OH:1])[CH:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 696002-Hydroxy-4-Methoxybenzaldehyde

Product 1

HCID 109535825-Methoxy-2-methylphenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-hydroxy-4-methoxy-benzaldehyde (30.4 g, 0.20 mol), palladium/carbon (10%, 50% water, 30 g), concentrated HCl (15 ml) in 1500 ml of ethyl acetate was hydrogenated at 50 psi, at room temperature overnight, then filtered through Celite®. The filtrate was washed with water, brine, dried over sodium sulfate, concentrated, and purified using normal phase chromatography. 400 MHz 1H NMR (CDCl3) δ 7.01 (d, 1H), 6.44-6.38 (m, 2H), 4.65 (s, 1H), 3.79 (s, 3H), 2.18 (s, 3H).

Workup

  1. filtrationfiltered through Celite®
  2. washThe filtrate was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified

Sources & evidence

ORD record
ord-0a38498ab8784b368eb9c29628035b87
Source dataset
uspto-grants-2004_12
Patent number
US06833380B2

Reaction notes

Loading…