Isobutylene → p-tert-Butoxyanisole

HRID 358309Notes

Reaction equation

HRID 358309 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[CH3:10][C:11](=[CH2:13])[CH3:12]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:11]([CH3:13])([CH3:12])[CH3:10])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 8255IsobutyleneHCID 90154-Methoxyphenol

Product 1

HCID 84881p-tert-ButoxyanisoleYield 70%

Conditions

Temperature
20 °C

Procedure

To a 300 cc stainless steel stirred autoclave may be added 124 g (1.0 mol) 4-methoxyphenol and 10 g of XN-1010, a cation exchange resin bearing sulfonic acid groups supplied by Rohm and Haas Co. The system may be charged with 56 g (1.0 mol) isobutylene and the mixture stirred 5 hours at 20° C. Resin may be removed by filtration and unreacted phenol may be removed by washing the filtrate with an aqueous solution of 10% sodium hydroxide. The organic material may be washed with water to remove caustic and dried with magnesium sulfate to afford t-butyl 4-methoxyphenyl ether in a yield of about 70%.

Workup

  1. customResin may be removed by filtration and unreacted phenol
  2. custommay be removed
  3. washby washing the filtrate with an aqueous solution of 10% sodium hydroxide
  4. washThe organic material may be washed with water
  5. customto remove caustic
  6. dry with materialdried with magnesium sulfate

Sources & evidence

ORD record
ord-6b00d6db55b84cc4a4ad6a25e0c8b88e
Source dataset
uspto-grants-1984_08
Patent number
US04465871

Reaction notes

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