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

HRID 1762662Notes

Reaction equation

HRID 1762662 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-b101681c0ff548128676520f8d555784
Source dataset
uspto-grants-1989_05
Patent number
US04833164

Reaction notes

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