Hydrochloric Acid → HCID 21424223, compound

HRID 259300Notes

Reaction equation

HRID 259300 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([CH3:16])[CH:5]=1)(=[O:3])[CH3:2].[CH3:17][Mg]I.[Mg].CI.Cl>CCOCC>[OH:3][C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([CH3:16])[CH:5]=1)([CH3:17])[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 5462224MagnesiumHCID 20562166HCID 20562166, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 21424223HCID 21424223, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of 4-acetyl-2-methylbiphenyl (12.8g, 0.061 mole) in dry ether (340me) was added over 30 minutes to methyl magnesium iodide, (from magnesium, 1.8g, methyl iodide, 5.1ml, and ether 61 ml). The mixture was stirred under reflux for 5 hours, stirred overnight at room temperature and finally decomposed by the dropwise addition of hydrochloric acid (2N; 170ml). The product was isolated in ether washed with aqueous sodium thiosulphate and water, dried, evaporated, and distilled. The product solidified on standing and was recrystallized from light petroleum (b.p. 40°-60° C) to give 4-(1-hydroxy-1-methylethyl)-2-methylbiphenyl, m.p. 60°-64° C. A solution of this (5g) in ethyl acetate (50ml) containing concentrated sulphuric acid (3 drops) was hydrogenated over palladium-charcoal (10%, 0.5g) for 8 hours. The mixture was filtered and the filtrate was concentrated by evaporation. The residue was dissolved in ether (50ml), washed with aqueous sodium hydrogen carbonate, dried, evaporated and distilled to give 4-isopropyl-2-methylbiphenyl, b.p. 93°-94° C/0.3mm.

Workup

  1. temperatureunder reflux for 5 hours
  2. stirringstirred overnight at room temperature
  3. washwashed with aqueous sodium thiosulphate and water
  4. customdried
  5. customevaporated
  6. distillationdistilled
  7. customwas recrystallized from light petroleum (b.p. 40°-60° C)

Sources & evidence

ORD record
ord-02226e1e8d3e44d191e92bc3c99076e4
Source dataset
uspto-grants-1977_07
Patent number
US04036989

Reaction notes

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