2-Methoxy-4-Methylphenol → HCID 22970609, compound

HRID 1060232Notes

Reaction equation

HRID 1060232 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][CH:4]=[C:3]([S:7](Cl)(=[O:9])=[O:8])[CH:2]=1.[CH3:12][O:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[OH:21].C(N(CC)CC)C>C(Cl)Cl>[CH3:11][C:1]1[CH:2]=[C:3]([S:7]([O:21][C:15]2[CH:16]=[CH:17][C:18]([CH3:20])=[CH:19][C:14]=2[O:13][CH3:12])(=[O:9])=[O:8])[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 71442-Methoxy-4-MethylphenolHCID 8471TriethylamineHCID 27345953-Methylbenzenesulphonyl chloride

Product 1

HCID 22970609HCID 22970609, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of m-toluenesulfonyl chloride (0.53 g, 2.78 mmol) and 2-methoxy-4-methylphenol (0.38 g, 2.75 mmol) in DCM (10 mL) was treated with triethylamine (0.5 mL,3.6 mmol) and stirred at ambient temperature. After 18 hours the reaction was concentrated in vacuo, the residue dissolved in 1:1 hexane:DCM, filtered, and the filtrate evaporated under high vacuum giving the title compound as a white solid (0.79 g, 99%). 1H NMR (300 MHz, CDCl3) δ 7.72 (br s, 1H), 7.66 (br d, 1H, J=7.2 Hz), 7.45 (br d, 1H,1J=7.2 Hz), 7.38 (t, 1H,=7.6 Hz), 7.00 (d, 1H,=8.1 Hz), 6.67 (m, 1H), 3.54 (s, 3H), 2.42 (s, 3H), 2.31 (s, 3H).

Workup

  1. concentrationAfter 18 hours the reaction was concentrated in vacuo
  2. dissolutionthe residue dissolved in 1:1 hexane
  3. filtrationDCM, filtered
  4. customthe filtrate evaporated under high vacuum

Sources & evidence

ORD record
ord-72eacfc3e9b34de0b885767332c3c32d
Source dataset
uspto-grants-2003_02
Patent number
US06521663B2

Reaction notes

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