Benzyl Bromide → 5-(Benzyloxy)-1,2,3,4-tetrahydronaphthalene

HRID 1719199Notes

Reaction equation

HRID 1719199 reaction equation
[C:1]1([OH:11])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O.CCOCC>[CH2:18]([O:11][C:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 682585,6,7,8-Tetrahydro-1-naphthol

Product 1

HCID 226476065-(Benzyloxy)-1,2,3,4-tetrahydronaphthaleneYield 99.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

5,6,7,8-tetrahydro-1-naphthol (5.9 g, 39mM) was added to a suspension of potassium carbonate (8.3 g, 60mM) in acetone (100 ml) and heated under reflux for 0.5 hour. Benzyl bromide (7.5 g, 43.8mM) was then added and the mixture was heated under reflux for a further 3 days with stirring. The resulting suspension was filtered and the filtrate was evaporated under reduced pressure to give an oil. This oil was dissolved in ether, washed with water, dried (sodium sulphate) and evaporated to giving an oil which was distilled under high vacuum to give the benzyl ether (3) (9.4 g, b.p. 170°-176° C. at 0.8 mm Hg).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 0.5 hour
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for a further 3 days
  5. filtrationThe resulting suspension was filtered
  6. customthe filtrate was evaporated under reduced pressure
  7. customto give an oil
  8. washwashed with water
  9. dry with materialdried (sodium sulphate)
  10. customevaporated
  11. customto giving an oil which
  12. distillationwas distilled under high vacuum

Sources & evidence

ORD record
ord-ac8df157aa654bf7a11ea1c6e40d18fe
Source dataset
uspto-grants-1985_09
Patent number
US04539319

Reaction notes

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