Diethyl Ether → 1-Butyl-2-methylnaphthalene

HRID 1729835Notes

Reaction equation

HRID 1729835 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][CH2:13][CH2:14][CH3:15])=[C:4]([CH3:16])[CH:3]=1.ClCC1C2C(=CC=CC=2)C=CC=1C.C(Br)CC.CCOCC>C1(C)C=CC=CC=1>[CH2:12]([C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:2]=[CH:3][C:4]=1[CH3:16])[CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 78401-BromopropaneHCID 811061-Chloromethyl-2-methylnaphthaleneHCID 215014121-Bromo-4-butyl-3-methylnaphthalene

Product 1

HCID 30160301-Butyl-2-methylnaphthalene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Bromo-4-butyl-3-methylnaphthalene-- A solution of 1-chloromethyl-2-methylnaphthalene (32.3 g) in dry toluene (150 ml) was dropwise added to a Grignard reagent, from n-propylbromide (27.1 g), Mg(5.3 g), and dry ether (150 ml). The ether was evaporated, and the resulting solution was refluxed for 2 hrs. The reaction mixture was cooled and poured into an ice-cooled aqueous ammonium chloride. The organic layer was taken, and aqueous layer was extracted with ether. Combined organic solution was washed with 10% HCl, 10% NaOH, and water and dried. The solvent was evaporated, and the residue was distilled to give an oil (8.8 g) of 1-butyl-2-methylnaphthalene, bp2 82°-86° C. The oil (8.8 g) was brominated by a similar manner given in Example 9 to afford an oil (8.0 g, 65.1%) of bp2 124°-128° C.

Workup

  1. customThe ether was evaporated
  2. temperaturethe resulting solution was refluxed for 2 hrs
  3. temperatureThe reaction mixture was cooled
  4. additionpoured into an ice-
  5. temperaturecooled aqueous ammonium chloride
  6. extractionaqueous layer was extracted with ether
  7. washCombined organic solution was washed with 10% HCl, 10% NaOH, and water
  8. customdried
  9. customThe solvent was evaporated
  10. distillationthe residue was distilled

Sources & evidence

ORD record
ord-7704256ee4b7499180e4da0121d5984c
Source dataset
uspto-grants-1976_11
Patent number
US03989746

Reaction notes

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