1-Tetralone → 4-(3-Methoxyphenyl)-1,2-dihydronaphthalene

HRID 1464002Notes

Reaction equation

HRID 1464002 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH2:10]1[CH2:20][C:18](=O)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11]1>C1COCC1.CCOCC>[CH3:9][O:8][C:4]1[CH:3]=[C:2]([C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:18][CH2:20][CH:10]=2)[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 107241-TetraloneHCID 169713-Bromoanisole

Product 1

HCID 150694194-(3-Methoxyphenyl)-1,2-dihydronaphthalene

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the Grignard reagant derived from 50 g (0.27 mol) of 3-bromoanisole in 200 ml of dry THF was treated with a solution of alpha-tetralone in 100 ml of THF added over 1 hour while maintaining the internal temperature at 15°-25° C. After stirring overnight, the mixture was diluted with 500 ml of ether and quenched with 200 ml of 20% aqueous ammonium chloride. The aqueous layer was extracted with 200 ml of ether. The combined organic layers were dried over MgSO4 and evaporated to 66.5 g of the oily alcohol. This was dissolved in 450 ml of dry toluene containing 0.020 g of p-toluenesulfonic acid and refluxed overnight in a Dean-Stark apparatus. After cooling, the mixture was washed with 100 ml of 5% sodium bicarbonate, with 100 ml of water, and then with 100 ml of brine. The mixture was dried over MgSO4 and evaporated. The residue was distilled under reduced pressure to give the title compound, b.p. (0.5 mm) 158°-162° C.

Workup

  1. additionadded over 1 hour
  2. temperaturewhile maintaining the internal temperature at 15°-25° C
  3. customquenched with 200 ml of 20% aqueous ammonium chloride
  4. extractionThe aqueous layer was extracted with 200 ml of ether
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. customevaporated to 66.5 g of the oily alcohol
  7. dissolutionThis was dissolved in 450 ml of dry toluene containing 0.020 g of p-toluenesulfonic acid
  8. temperaturerefluxed overnight in a Dean-Stark apparatus
  9. temperatureAfter cooling
  10. washthe mixture was washed with 100 ml of 5% sodium bicarbonate, with 100 ml of water
  11. dry with materialThe mixture was dried over MgSO4
  12. customevaporated
  13. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-c75409cff9f9459fb7666682fa90d1d2
Source dataset
uspto-grants-1994_04
Patent number
US05302716

Reaction notes

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