Sulfuric Acid → HCID 22063473, compound

HRID 12096Notes

Reaction equation

HRID 12096 reaction equation
S(=O)(=O)(O)O.[CH2:6]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([CH3:18])(O)[CH3:16])=[CH:10][CH:9]=1)[CH3:7].[C:19](#[N:21])[CH3:20].[OH-:22].[Na+]>C(O)(=O)C>[CH2:6]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([NH:21][C:19](=[O:22])[CH3:20])([CH3:18])[CH3:16])=[CH:10][CH:9]=1)[CH3:7]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 22063451HCID 22063451, compound

Product 1

HCID 22063473HCID 22063473, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6.2 mL of concentrated sulfuric acid is added dropwise to 15.5 g (87 mmol) of 1-(4-ethylphenyl)-2-methylpropan-2-ol in 4.8 mL (91 mmol) acetonitrile and 15 mL glacial acetic acid within 15 minutes, during which time the temperature rises to 65° C. It is then stirred for one hour, diluted with ice water, and made alkaline with concentrated sodium hydroxide solution. After another 30 minutes' stirring, the solid precipitated is suction filtered and washed with water. The crude product is dissolved in ethyl acetate, dried with sodium sulfate, and evaporated down. The oil remaining is combined with petroleum ether, whereupon a solid is precipitated which is filtered off and dried. Yield: 16.3 g (85%); melting point 90° C.-92° C.

Workup

  1. customrises to 65° C
  2. stirringAfter another 30 minutes' stirring
  3. customthe solid precipitated
  4. filtrationfiltered
  5. washwashed with water
  6. dissolutionThe crude product is dissolved in ethyl acetate
  7. dry with materialdried with sodium sulfate
  8. customevaporated down
  9. customis precipitated which
  10. filtrationis filtered off
  11. customdried

Sources & evidence

ORD record
ord-c2a674e1238f4dc8b04cc0d29f019f60
Source dataset
uspto-grants-2010_06
Patent number
US07727984B2

Reaction notes

Loading…