O-Cresol → Benzene, 1-methyl-2-(1-methylethoxy)-

HRID 2049897Notes

Reaction equation

HRID 2049897 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[CH:11](Br)([CH3:13])[CH3:12]>CS(C)=O>[C:1]1([CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=1[O:7][CH:11]([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 335O-CresolHCID 63582-BromopropaneHCID 14798Sodium Hydroxide

Product 1

HCID 141785Benzene, 1-methyl-2-(1-methylethoxy)-Yield 71.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of 54.1 g (0.5 mol) of ortho-cresol in 150 ml of DMSO was added portionwise and with stirring 12 g of 57% sodium hydroxide. This addition was exothermic to 45° C. After 2 hours at ambient temperature, 61.5 g (0.5 mol) of isopropyl bromide in 50 ml of DMSO was added dropwise with stirring. After another 2 hours, the reaction mixture was poured into 1000 ml of ice water and extracted with ether. Distillation of the dried extract gave 53.9 g of product as a colorless liquid; b.p. 94°-96° C. (30 mm).

Workup

  1. additionThis addition
  2. customwas exothermic to 45° C
  3. waitAfter another 2 hours
  4. extractionextracted with ether
  5. distillationDistillation of the dried
  6. extractionextract

Sources & evidence

ORD record
ord-5eaa8e70950247eeb24560413c9b601d
Source dataset
uspto-grants-1980_04
Patent number
US04199347

Reaction notes

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