1-Methoxynaphthalene → 2-(4-Chlorobutyl)-1-methoxynaphthalene

HRID 1165026Notes

Reaction equation

HRID 1165026 reaction equation
C([Li])CCC.[CH3:6][O:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1.Br[CH2:19][CH2:20][CH2:21][CH2:22][Cl:23].[Cl-].[NH4+]>C1CCCCC1>[Cl:23][CH2:22][CH2:21][CH2:20][CH2:19][C:9]1[CH:10]=[CH:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]=1[O:7][CH3:6]

Participants

6

Reactant 4

HCID 166681-MethoxynaphthaleneHCID 25517Ammonium ChlorideHCID 813641-Bromo-4-chlorobutaneHCID 178418339Butyllithium

Product 1

HCID 156179372-(4-Chlorobutyl)-1-methoxynaphthaleneYield 39%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent2×

Procedure

A solution of N,N,N',N'-tetramethylenediamine (18.12 mL, 0.120 mole) in cyclohexane (36 mL) was treated with n-butyllithium (1.55M in hexane; 79.8 mL, 0.123 mole) at room temperature. A solution of 1-methoxynaphthalene (17.4 mL, 0.120 mole) in cyclohexane (20 mL) was added over 30 minutes, and the resulting solution was stirred for 1.5 hours. It was then cooled to 0°, and 1-bromo-4-chlorobutane (27.0 mL, 0.234 mole) was added over 15 minutes. The mixture was warmed to room temperature and stirred for 17 hours, then poured into saturated aqueous ammonium chloride and extracted with ethyl acetate. The crude product was chromatographed with 98:2 hexane/ether to provide the title compound (11.60 g, 39%) as a pale yellow oil.

Workup

  1. temperatureIt was then cooled to 0°
  2. stirringstirred for 17 hours
  3. extractionextracted with ethyl acetate
  4. customThe crude product was chromatographed with 98:2 hexane/ether

Sources & evidence

ORD record
ord-f7d5aacd16be49b6b51b6f5be21e624a
Source dataset
uspto-grants-1990_03
Patent number
US04906636

Reaction notes

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