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

HRID 2081361Notes

Reaction equation

HRID 2081361 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)phenol

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-hydroxybutyl) phenol (Compound 39) 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-d1566dbd766a405d99fccb20423664c6
Source dataset
uspto-grants-1993_02
Patent number
US05183827

Reaction notes

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