Phenol → 5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1265243Notes

Reaction equation

HRID 1265243 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:9]([CH3:17])([CH2:11][C:12](Cl)(C)[CH2:13][CH3:14])[CH3:10].[Cl-].[Al+3].[Cl-].[Cl-].Cl[CH2:23]Cl>>[CH3:17][C:9]1([CH3:10])[CH2:11][CH2:12][C:13]([CH3:14])([CH3:23])[C:5]2[CH:6]=[C:1]([OH:7])[CH:2]=[CH:3][C:4]1=2

Participants

5

Reactant 4

HCID 996PhenolHCID 6344DichloromethaneHCID 6451240Aluminum(III) ChlorideHCID 12644949HCID 12644949, compound

Product 1

HCID 2687865,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-olYield 83%

Procedure

A 200 mL round-bottomed flask equipped with stir bar was charged with a solution of phenol (10.2 g, 108 mmol) and 2,4-dichloro-2,4-dimethylhexane (21.8 g, 119 mmol) in dichloromethane (50 mL) at 0° C. Aluminum chloride (1.44 g, 10.8 mmol) was added slowly to the solution until the spontaneous reflux had subsided and the solution became pale orange in color. After stirring 10-15 min at 0° C., the reaction was poured into ice water (30 mL) and the layers were separated. The aqueous layer was extracted with EtOAc (2×30 mL). The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated to give a pale yellow/white solid. Recrystallization from hexanes gave the product 5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-ol 18.25 g (83%) as a white crystalline solid: 1H-NMR (400MHz, CDCl3) δ 7.17 (d, J=8.5 Hz, 1H, Ar-H), 6.76 (d, J=3.0 Hz, 1Hz, Ar-H), 6.62 (dd, J=8.5 Hz, 3.0 Hz, 1H, Ar-H), 4.52 (s, 1H, OH), 1.65 (s, 4H, 2CH2), 1.26 (s, 6H, 2CH3), 1.24 (s, 6H, 2CH3).

Workup

  1. customA 200 mL round-bottomed flask equipped
  2. temperaturespontaneous reflux
  3. stirringAfter stirring 10-15 min at 0° C.
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with EtOAc (2×30 mL)
  6. washThe combined organic extracts were washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a pale yellow/white solid
  11. customRecrystallization from hexanes

Sources & evidence

ORD record
ord-3efe89711583462fac9012dec921d3bc
Source dataset
uspto-grants-2003_04
Patent number
US06545049B1

Reaction notes

Loading…