3-Methylcatechol → 5-tert-Butyl-3-methylpyrocatechol

HRID 1892632Notes

Reaction equation

HRID 1892632 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[C:3]=1[OH:9].[C:10](O)([CH3:13])([CH3:12])[CH3:11].S(=O)(=O)(O)O>CCCCCCC>[C:10]([C:7]1[CH:6]=[C:4]([OH:5])[C:3]([OH:9])=[C:2]([CH3:1])[CH:8]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 3403-MethylcatecholHCID 1118Sulfuric AcidHCID 6386tert-Butanol

Product 1

HCID 751735-tert-Butyl-3-methylpyrocatecholYield 99.9%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
80 °C

Procedure

A 1000 mL three neck flask equipped with stirrer, condenser and thermometer is charged with 3-methylcatechol (25.0 g, 0.20 mole), tert-butanol (38.0 mL, 0.40 mole) and 500 mL of heptane; followed by addition of sulfuric acid (98%, 20 g) slowly. The mixture is heated to 80° C. for 6 hrs until gas chromatography (GC) indicates the completion of the reaction. The solvent is removed in vacuo, and the residue is dissolved in CH2Cl2 and washed with water, NaHCO3 (aq.), brine and dried (Na2SO4). Filtration and concentration yield 5-tert-butyl-3-methylcatechol (36 g, 84%). 1H NMR: 6.79 (s, 1H), 6.75 (s, 1H), 5.01 (br, 1H), 2.29 (s, 3H), 1.29 (s, 9H).

Workup

  1. customthe completion of the reaction
  2. customThe solvent is removed in vacuo
  3. dissolutionthe residue is dissolved in CH2Cl2
  4. washwashed with water, NaHCO3 (aq.), brine
  5. dry with materialdried (Na2SO4)
  6. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-9083ec8df1d74131812b051c63d01ca3
Source dataset
uspto-grants-2013_08
Patent number
US08507717B2

Reaction notes

Loading…