Toluene → 4-cyclopropylphenol

HRID 973048Notes

Reaction equation

HRID 973048 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](O)=[C:4]([CH:9]2[CH2:11][CH2:10]2)[C:3]=1Br.C1(C)C=CC=CC=1.C[O:21]CCO[AlH2-]OCCOC.[Na+]>C1C=CC=CC=1>[CH:9]1([C:4]2[CH:5]=[CH:6][C:7]([OH:21])=[CH:2][CH:3]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 16684438Red-AlHCID 53992661HCID 53992661, compound

Product 1

HCID 109862774-cyclopropylphenol

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In a 500 ml flask equipped with a reflux condenser, and magnetic stirring bar under a nitrogen atmosphere were placed 11 g (37.6 moles) of dibromocyclopropylphenol, 100 ml of toluene, and 50 g of 70% solution of "Red-Al" [sodium bis(2-methoxyethoxy aluminum hydride)] in benzene. The solution was then heated to reflux for 6 hours and allowed to stir overnight at room temperature. The reaction was then quenched with water and acidified with concentrated hydrochloric acid. The layers were separated and the aqueous layer extracted with 100 ml of ether. The organic layers were combined and washed with dilute base. The water layer was then acidified with concentrated hydrochloric acid and extracted with methylene dichloride. The methylene dichloride extract was dried over anhydrous magnesium sulfate and the solvent evaporated. A yield of 3 g of 4-cyclopropylphenol, an amber oil, was obtained.

Workup

  1. customIn a 500 ml flask equipped with a reflux condenser, and magnetic stirring bar under a nitrogen atmosphere
  2. temperatureThe solution was then heated
  3. temperatureto reflux for 6 hours
  4. customThe reaction was then quenched with water
  5. customThe layers were separated
  6. extractionthe aqueous layer extracted with 100 ml of ether
  7. washwashed
  8. additionwith dilute base
  9. extractionextracted with methylene dichloride
  10. extractionThe methylene dichloride extract
  11. dry with materialwas dried over anhydrous magnesium sulfate
  12. customthe solvent evaporated

Sources & evidence

ORD record
ord-57a69b443c654b8ab0fa5323df511d00
Source dataset
uspto-grants-1977_10
Patent number
US04054667

Reaction notes

Loading…