4,4-Dimethyl-1,2,3,4-tetrahydronaphthalen-1-ol → 1,2-Dihydro-1,1-dimethylnaphthalene

HRID 381538Notes

Reaction equation

HRID 381538 reaction equation
[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5](O)[CH2:4][CH2:3]1>C(O)(=O)C(O)=O.O>[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH2:3]1

Participants

4

Reactant 1

HCID 126430324,4-Dimethyl-1,2,3,4-tetrahydronaphthalen-1-ol

Product 1

HCID 127728391,2-Dihydro-1,1-dimethylnaphthalene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 971Oxalic AcidSolvent

Procedure

A mixture of 1,2,3,4-tetrahydro-4,4-dimethyl-1-naphthol (9.6 g, 54.5 mmoles) in 20% aqueous oxalic acid was stirred and heated to reflux for 5 hours. After cooling, the reaction mixture was diluted with one volume of water and then extracted with one volume of ether. The aqueous layer was extracted again with one volume of ethyl acetate and the combined organic phases were dried over magnesium sulfate, filtered, and evaporated under reduced pressure to leave an oil which was purified using silica gel column chromatography, eluting with ethyl acetate:hexane (0.1:49.9) to give 1,2-dihydro-1,1-dimethylnaphthalene as a colorless oil. (4.76 g, 55%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 hours
  3. temperatureAfter cooling
  4. extractionextracted with one volume of ether
  5. extractionThe aqueous layer was extracted again with one volume of ethyl acetate
  6. dry with materialthe combined organic phases were dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customto leave an oil which
  10. customwas purified
  11. washeluting with ethyl acetate:hexane (0.1:49.9)

Sources & evidence

ORD record
ord-75bbf76b78c84f09bd562d4ffc40d68c
Source dataset
uspto-grants-2001_10
Patent number
US06306865B1

Reaction notes

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