Water → {[(1-Chlorononan-4-yl)oxy]methyl}benzene

HRID 1439475Notes

Reaction equation

HRID 1439475 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:8][CH2:9][CH2:10][CH2:11][CH:12]([O:18][CH2:19]Cl)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].O>CCOCC>[Cl:8][CH2:9][CH2:10][CH2:11][CH:12]([O:18][CH2:19][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 7961Bromobenzene2×HCID 213974091-Chloro-4-(chloromethoxy)nonane

Product 1

HCID 21397378{[(1-Chlorononan-4-yl)oxy]methyl}benzeneYield 85.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of bromobenzene (13.18 g., 0.084 mole) in ether (50 ml.) is added to a suspension of Mg (2.04 g., 0.084 mole) in ether (50 ml.) dropwise so as to maintain a gentle reflux. After complete addition of the bromobenzene, the mixture is heated on a steam bath for an additional hour. The reaction mixture is then cooled to 5°-10° C. by means of an ice-water bath, and 1-chloro-4-chloromethoxynonane (19.05 g., 0.084 mole) is added dropwise over 15 minutes. The resulting suspension is stirred for 18 hours at room temperature. The reaction mixture is diluted with ether (100 ml.), cooled to 0°-5° C., and cold water (75 ml.) is added with vigorous stirring while the temperature is kept below 5° C. Let stir at 0°-5° C. for about 15 minutes. The aqueous phase is separated from the ether phase (A), and the aqueous layer is extracted with ether (150 ml., B). Organic solution A is combined with B, washed with H2O (100 ml.), 5% K2CO3 (100 ml.), again with H2O (100 ml.), finally with saturated NaCl solution, and is dried over anhydrous Na2SO4. Removal of the solvent in vacuo yields 1-chloro-4-benzyloxynonane (19.28 g., 0.072 mole, 85.7% yield).

Workup

  1. temperatureto maintain a gentle reflux
  2. temperaturethe mixture is heated on a steam bath for an additional hour
  3. temperatureThe reaction mixture is then cooled to 5°-10° C. by means of an ice-water bath
  4. temperaturecooled to 0°-5° C.
  5. stirringwith vigorous stirring while the temperature
  6. customis kept below 5° C
  7. stirringLet stir at 0°-5° C. for about 15 minutes
  8. customThe aqueous phase is separated from the ether phase (A)
  9. extractionthe aqueous layer is extracted with ether (150 ml., B)
  10. washwashed with H2O (100 ml.), 5% K2CO3 (100 ml.), again with H2O (100 ml.), finally with saturated NaCl solution
  11. dry with materialis dried over anhydrous Na2SO4
  12. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-84d579aa3226485e8f698097cfecd625
Source dataset
uspto-grants-1977_11
Patent number
US04059601

Reaction notes

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