Sulfuric Acid → 1-(5-tert-Butyl-2,4-dihydroxyphenyl)ethan-1-one

HRID 2097279Notes

Reaction equation

HRID 2097279 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]([C:9]1[CH:10]=[CH:11][C:12]([OH:16])=[CH:13][C:14]=1[OH:15])=[O:8].[CH3:17][C:18](O)([CH3:20])[CH3:19]>FC(F)(F)C(O)=O>[C:18]([C:11]1[C:12]([OH:16])=[CH:13][C:14]([OH:15])=[C:9]([C:7](=[O:8])[CH3:6])[CH:10]=1)([CH3:20])([CH3:19])[CH3:17]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 69902',4'-Dihydroxyacetophenone

Product 1

HCID 157472661-(5-tert-Butyl-2,4-dihydroxyphenyl)ethan-1-oneYield 92.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Sulphuric acid (4 ml, 75 mmol) was added to a suspension of 2,4-dihyroxyacetophenone (22.8 g, 150 mmol) in a mixture of 2-methyl-2-propanol (35 g, 470 mmol) and trifluoroacetic acid (80 ml), under a nitrogen atmosphere. The resulting suspension was heated, oil bath temperature 75° C., for ˜3 hrs. to give a pale red solution. The resulting solution was allowed to cool and poured into ice/water (350 ml), to give a pale pink precipitate. The solids were removed by filtration and washed with water (600 ml) and hexane (200 ml) to give a pale pink powder. Dried in vacuo (40° C.), to give 1-(5-tert-butyl-2,4-dihydroxy-phenyl)-ethanone as a pale orange powder (28.8 g, 92%).

Workup

  1. temperatureThe resulting suspension was heated
  2. customto give a pale red solution
  3. temperatureto cool
  4. customto give a pale pink precipitate
  5. customThe solids were removed by filtration
  6. washwashed with water (600 ml) and hexane (200 ml)
  7. customto give a pale pink powder
  8. customDried in vacuo (40° C.)

Sources & evidence

ORD record
ord-613f8207f88f42b9b4e29fc9e946cb74
Source dataset
uspto-grants-2013_05
Patent number
US08450310B2

Reaction notes

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