O-Cresol → 3-tert-Butyl-2-methylphenol

HRID 1953927Notes

Reaction equation

HRID 1953927 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.C=[CH:15][CH2:16][CH3:17].[CH3:18]C=CC.[OH-].[Na+]>>[C:16]([C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([OH:7])[C:1]=1[CH3:8])([CH3:15])([CH3:17])[CH3:18]

Participants

6

Reactant 5

HCID 335O-Cresol2×HCID 1118Sulfuric Acid3×HCID 78441-ButeneHCID 12220But-2-eneHCID 14798Sodium Hydroxide2×

Product 1

HCID 137519873-tert-Butyl-2-methylphenol

Procedure

Into a reaction vessel equipped with a stirrer, gas blowing tube, thermometer and condenser is fed cresol into which sulfuric acid has been dissolved (sulfuric acid is dissolved in 1.2% by weight based on 100% by weight of cresol) at 795 g/hr, further, butylation reaction is conducted for 8 hours at 65° C. under normal pressure with blowing in an isobutyrene mixed gas containing 1-butene, 2-butene and the like, and the resulted butylated reaction mixture is neutralized with an aqueous NaOH solution. For the neutralization, 1.5 equivalent NaOH is added per charged sulfuric acid and the treatment is conducted for 3 hours at 110° C., then an aqueous layer is separated, and the resulted oil layer is washed with water to obtain 11.79 kg of t-butylcresol mixture (cresolcontent6.4%, 4M2B contentl6.3%, 3M6B content 13.3%, dibutylated isomer content 58.6%, content of other components 5.4%).

Workup

  1. customInto a reaction vessel equipped with a stirrer
  2. dissolutionhas been dissolved
  3. customfurther, butylation reaction
  4. additionmixed gas
  5. customthe like, and the resulted
  6. customreaction mixture
  7. waitthe treatment is conducted for 3 hours at 110° C.
  8. customan aqueous layer is separated
  9. washthe resulted oil layer is washed with water

Sources & evidence

ORD record
ord-adfea41d6ad74e42aa50aabf3227ec6a
Source dataset
uspto-grants-2000_09
Patent number
US06120653

Reaction notes

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