Sulfuric Acid → 2,2,4,4-Tetramethylchroman

HRID 862261Notes

Reaction equation

HRID 862261 reaction equation
[CH3:1][C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])([CH3:8])[CH2:3][C:4]([CH3:7])(O)[CH3:5].OS(O)(=O)=O>O>[CH3:7][C:4]1([CH3:5])[CH2:3][C:2]([CH3:1])([CH3:8])[C:9]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[O:15]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 156611212-(1,1,3-Trimethyl-3-hydroxybutyl)phenol2×

Product 1

HCID 156611252,2,4,4-Tetramethylchroman

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.98 g (14.3 mmol) of 2-(1,1,3-trimethyl-3-hydroxybutyl) phenol (Compound 83) and 40 ml of 20% aqueous H2SO4 was heated at reflux, under nitrogen, for 4 h. The mixture was stirred at room temperature for a further 72 h and then diluted with 50 ml of water. The mixture was extracted with 3×20 ml of hexanes. The organic extracts were then combined and washed successively with water and saturated NaCl solution and then dried (MgSO4). The solvent was then removed in vacuo to give the title compound as a colorless oil. PMR (CDCl3): & 1.36 (6H, s), 1.37 (6H, s), 1.83 (2H, s), 6.71 (1H, dd, J-8.2 Hz, 1.5 Hz) 6.92 (1H, td, J~8.2 Hz, 1.5 Hz), 7.09 (1H, td, J-8.2 Hz, 1.5 Hz), 7.29 (1H, dd, J~8.2 Hz, 1.5 Hz).

Workup

  1. temperaturewas heated
  2. temperatureat reflux, under nitrogen, for 4 h
  3. extractionThe mixture was extracted with 3×20 ml of hexanes
  4. washwashed successively with water and saturated NaCl solution
  5. dry with materialdried (MgSO4)
  6. customThe solvent was then removed in vacuo

Sources & evidence

ORD record
ord-c6b2f63189484d4285893cc94b613f0b
Source dataset
uspto-grants-1998_02
Patent number
US05717094

Reaction notes

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