2-Ethyl-5-methylphenol → 5-Ethyl-4-hydroxy-2-methyl-benzaldehyde

HRID 858856

Reaction equation

HRID 858856 reaction equation
[CH3:1][O:2]C(Cl)Cl.[CH2:6]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=1[OH:15])[CH3:7]>[Ti](Cl)(Cl)(Cl)Cl>[CH2:6]([C:8]1[C:9]([OH:15])=[CH:10][C:11]([CH3:14])=[C:12]([CH:13]=1)[CH:1]=[O:2])[CH3:7]

Participants

4

Reactant 2

HCID 155232-Ethyl-5-methylphenolHCID 21004Methane, dichloromethoxy-

Product 1

HCID 587624205-Ethyl-4-hydroxy-2-methyl-benzaldehydeYield 50%

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

Titanium(IV) chloride (11 mL, 11 mmol, 1M in CH2Cl2) followed by dichloromethyl methyl ether (1.04 g, 9.1 mmol) was added to a cooled 0° C. solution of 2-ethyl-5-methyl-phenol (0.75 g, 5.5 mmol) The reaction mixture was stirred for 30 mins and then warmed up to rt and stirred for another 30 mins. The mixture was poured into ice and extracted with EtOAc. The organic layers were washed with satd NaHCO3, brine, dried over Na2SO4 and concentrated to a purple oil. Purification by flash column chromatography (0% to 10% EtOAc in hexanes) gave the title compound as an oil (0.45 g, 50%). 1H NMR (400 MHz, CDCl3): δ 1.26 (t, J=7.6 Hz, 3 H), 2.60 (s, 3 H), 2.65 (q, J=7.6 Hz, 2 H), 5.37 (s, 1 H), 6.62 (s, 1 H), 7.62 (s, 1 H), 10.11 (s, 1 H).

Workup

  1. stirringstirred for another 30 mins
  2. additionThe mixture was poured into ice
  3. extractionextracted with EtOAc
  4. washThe organic layers were washed with satd NaHCO3, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to a purple oil
  7. customPurification by flash column chromatography (0% to 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-6f200c5e6a834706a8edd9a9a298e498
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Linked notes

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