4-tert-Butylphenol → 1-(Allyloxy)-4-tert-butylbenzene

HRID 375587Notes

Reaction equation

HRID 375587 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].Cl[CH2:13][CH:14]=[CH2:15].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH3:4][C:2]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:15][CH:14]=[CH2:13])=[CH:9][CH:10]=1)([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 73934-tert-ButylphenolHCID 7850Allyl chlorideHCID 11430Potassium Carbonate

Product 1

HCID 6001241-(Allyloxy)-4-tert-butylbenzene

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 45 g 4-(1,1-dimethylethyl)phenol, 30 g 3-chloro-1-propene, 50 g anhydrous potassium carbonate and 250 ml 2-butanone was refluxed for 15 hours, after which time the solvent was removed in a rotary evaporator. Water was added to dissolve the potassium salts and the product extracted twice with ether. The ether layer was dried, removed, and the product distilled. The 50 grams of 1-(1,1-dimethylethyl)-4-(2-propenyloxy)benzene was found to boil at 70°-75° C. at 0.2 mm Hg, listed in Table 1 as compound I-4)

Workup

  1. temperaturewas refluxed for 15 hours
  2. customafter which time the solvent was removed in a rotary evaporator
  3. additionWater was added
  4. dissolutionto dissolve the potassium salts
  5. extractionthe product extracted twice with ether
  6. dry with materialThe ether layer was dried
  7. customremoved
  8. distillationthe product distilled
  9. customto boil at 70°-75° C. at 0.2 mm Hg

Sources & evidence

ORD record
ord-a451815d4b3a4939b1c7aca8fb4fc062
Source dataset
uspto-grants-1996_01
Patent number
US05486533

Reaction notes

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