Sulfuric Acid → 2-Ethyl-6-methylphenol

HRID 1958789Notes

Reaction equation

HRID 1958789 reaction equation
OS(O)(=O)=O.[CH2:6]([C:8]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:9]=1N)[CH3:7].N([O-])=[O:17].[Na+]>O>[CH2:6]([C:8]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:9]=1[OH:17])[CH3:7]

Participants

5

Reactant 3

HCID 1118Sulfuric Acid2×HCID 324852-Ethyl-6-methylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 5193332-Ethyl-6-methylphenolYield 56.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To an ice-cold solution of H2SO4 (150 mL) in water (250 mL), 2-ethyl-6-methylaniline (15.0 g, 111 mmol) is added. The solution is treated with ice (150 g) before a solution of NaNO2 (10.7 g, 155 mmol) in water (150 mL) and ice (50 g) is added dropwise. The mixture is stirred at 0° C. for 1 h. 50% aq. H2SO4 (200 mL) is added and stirring is continued at rt for 18 h. The mixture is extracted with DCM, the org. extracts are dried over MgSO4 and evaporated. The crude product is purified by CC on silica gel eluting with Hept:EA 9:1 to give 2-ethyl-6-methyl-phenol as a crimson oil (8.6 g). LC-MS: tR=0.89 min; 1H NMR (CDCl3): δ 7.03-6.95 (m, 2H), 6.80 (t, J=7.6 Hz, 1H), 4.60 (s, 1H), 2.64 (q, J=7.6 Hz, 2H), 2.25 (s, 3H), 1.24 (t, J=7.6 Hz, 3H).

Workup

  1. additionis added dropwise
  2. stirringstirring
  3. waitis continued at rt for 18 h
  4. extractionThe mixture is extracted with DCM
  5. dry with materialextracts are dried over MgSO4
  6. customevaporated
  7. customThe crude product is purified by CC on silica gel eluting with Hept

Sources & evidence

ORD record
ord-db84a26035b04e7e9a054a3b64d97e13
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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