Sulfuric Acid → 2,2-Dimethylchroman

HRID 1085029

Reaction equation

HRID 1085029 reaction equation
O[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([CH3:13])([OH:12])[CH3:11].OS(O)(=O)=O>O>[CH3:11][C:10]1([CH3:13])[CH2:9][CH2:8][C:3]2[C:4](=[CH:5][CH:6]=[CH:7][CH:2]=2)[O:12]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 27789532-(3-Hydroxy-3-methylbutyl)phenol2×

Product 1

HCID 1369362,2-Dimethylchroman

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 16 g (89 mmol) of 4-(2-hydroxyphenyl)-2-methyl-2-butanol, (Compound 55), 40 ml of conc. H2SO4 and 160 ml of water was heated at reflux for 4 hours. The mixture was cooled, diluted with 300 ml of water and extracted with 2×100 ml of hexane. The organic extracts were combined, washed successively with water and saturated NaCl solution and then dried. The solution was then filtered and the filtrate concentrated in-vacuo to give the title compound as a yellow oil. PMR (CDCl3) : & 1.32 (6H, s), 1.78 (2H, t, J~6.8 Hz), 2.76 (2H, t, J~6.8 Hz), 6.74-6.85 (2H, m), 7.01-7.12 (2H, m).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. temperatureThe mixture was cooled
  4. extractionextracted with 2×100 ml of hexane
  5. washwashed successively with water and saturated NaCl solution
  6. customdried
  7. filtrationThe solution was then filtered
  8. concentrationthe filtrate concentrated in-vacuo

Sources & evidence

ORD record
ord-42af04ddd8e34408b68aebbf1deaf66a
Source dataset
uspto-grants-1991_04
Patent number
US05006550

Linked notes

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