Hydrochloric Acid → HCID 19706015, compound

HRID 727460Notes

Reaction equation

HRID 727460 reaction equation
O[CH2:2][C:3]1[C:8]([OH:9])=[C:7]([CH3:10])[CH:6]=[C:5]([CH3:11])[CH:4]=1.[C:12]([C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[OH:23])([CH3:15])([CH3:14])[CH3:13].[OH-].[Na+].Cl>O>[OH:23][C:17]1[C:16]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:21][C:20]([CH3:22])=[CH:19][C:18]=1[CH2:10][C:7]1[CH:6]=[C:5]([CH3:11])[CH:4]=[C:3]([CH3:2])[C:8]=1[OH:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 170042-tert-Butyl-4-methylphenolHCID 114805504397-13-1

Product 1

HCID 19706015HCID 19706015, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

In a 300 ml eggplant-type flask equipped with a Dimroth condenser, 10.4 g (0.068 mol) of intermediate 6-(hydroxymethyl)-2,4-dimethylphenol and 11.6 g (0.071 mol) of 2-t-butyl-4-methylphenol were suspended in 50 ml of water. To this suspension, an aqueous solution having 10.3 g (0.26 mol) of sodium hydroxide dissolved in 50 ml of water, was added, and the mixture was stirred by a magnetic stirrer. This mixture was heated to 100° C. and stirred at that temperature for 12 hours. The reaction mixture was cooled to room temperature, then acidified by concentrated hydrochloric acid and extracted with toluene. The obtained toluene solution was washed with water and then dried over anhydrous magnesium sulfate. From the solution having the anhydrous magnesium sulfate removed, toluene was distilled off, and the obtained residue was separated by silica gel chromatography to obtain 10.6 g (0.036 mol, yield: 51.9%) of (2-hydroxy-3-t-butyl-5-methylphenyl)-(2-hydroxy-3,5-dimethylphenyl)methane as a brown highly viscous liquid. By 1HNMR, the liquid was confirmed to be the desired product.

Workup

  1. additionwas added
  2. stirringstirred at that temperature for 12 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionextracted with toluene
  5. washThe obtained toluene solution was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customremoved
  8. distillationtoluene was distilled off
  9. customthe obtained residue was separated by silica gel chromatography

Sources & evidence

ORD record
ord-c8d7a6c1c49b4eacae74d56d366d7afe
Source dataset
uspto-grants-1998_01
Patent number
US05712403

Reaction notes

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