Dimethyl Sulfoxide → HCID 64764771, compound

HRID 716472Notes

Reaction equation

HRID 716472 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].CS(C)=O.[OH-].[K+].[CH2:18](I)[CH:19]([CH3:21])[CH3:20]>>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH2:18][CH:19]([CH3:21])[CH3:20])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 69232-Tert-ButylphenolHCID 10556Isobutyl iodide3×HCID 14797Potassium Hydroxide

Product 1

HCID 64764771HCID 64764771, compound

Procedure

To a solution of 60.1 g (0.40 mol) 2-tert-butylphenol in 600 ml of DMSO 89.6 g (1.60 mol) of KOH and 147 g (0.80 mol) of isobutyl iodide were added. This mixture was stirred for 2 h at room temperature, then 73.6 g (0.40 mol) of isobutyl iodide was added. The resulting mixture was stirred for 1 h, and, again, then 73.6 g (0.40 mol) of isobutyl iodide was added. The formed mixture was stirred overnight at room temperature. The top layer was separated. To the bottom layer 5 liters of water was added, and some product was extracted with 2×250 ml of dichloromethane. The combined organic extract (including the separated top layer) was washed with 5×1 liter of water, dried over Na2SO4, and evaporated to dryness. The crude product (free of 2-tert-butylphenol) was obtained from the residue by flash chromatography on silica gel 60 (40-63 um; eluent: hexanes). Further on, this crude product was distillated to give pure 1-tert-butyl-2-isobutoxybenzene, b.p. 85-95° C./4 mm Hg. This procedure gave 44.9 g (54%) of the title product.

Workup

  1. stirringThe resulting mixture was stirred for 1 h
  2. stirringThe formed mixture was stirred overnight at room temperature
  3. customThe top layer was separated
  4. additionTo the bottom layer 5 liters of water was added
  5. extractionsome product was extracted with 2×250 ml of dichloromethane
  6. extractionThe combined organic extract (
  7. washwas washed with 5×1 liter of water
  8. dry with materialdried over Na2SO4
  9. customevaporated to dryness
  10. customThe crude product (free of 2-tert-butylphenol) was obtained from the residue by flash chromatography on silica gel 60 (40-63 um; eluent: hexanes)

Sources & evidence

ORD record
ord-b6a8cd71bdd946bcb5ca42ffd7e69440
Source dataset
uspto-grants-2015_11
Patent number
US09187583B2

Reaction notes

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