Diethyl Ether → 2-(4-Bromophenethyl)-benzyl alcohol

HRID 1288543Notes

Reaction equation

HRID 1288543 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.[Br:12][C:13]1[CH:31]=[CH:30][C:16]([CH2:17][CH2:18][C:19]2[CH:29]=[CH:28][CH:27]=[CH:26][C:20]=2[C:21](OCC)=[O:22])=[CH:15][CH:14]=1.[Cl-].[NH4+]>C(OCC)(=O)C>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][CH2:18][C:19]2[CH:29]=[CH:28][CH:27]=[CH:26][C:20]=2[CH2:21][OH:22])=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydride2×HCID 21502882Ethyl 2-(4-bromophenethyl)-benzoate

Product 1

HCID 543373022-(4-Bromophenethyl)-benzyl alcohol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Lithium aluminum hydride, 3.8 g. (0.1 mole), is wegihed under nitrogen, transferred to a dry, nitrogen-flushed reaction flask, and suspended in 300 ml. of absolute ether. The mixture is stirred at reflux for 30 minutes and then, after cooling to room temperature, a solution of 36.16 g. (0.108 mole) of ethyl 2-(4-bromophenethyl)-benzoate in 100 ml. of absolute ether is added dropwise. The mixture is stirred at room temperature overnight. The excess lithium aluminum hydride is decomposed by the addition of 5 ml. of ethyl acetate and the mixture then is hydrolyzed by the addition of 30 ml. of saturated ammonium chloride solution. The ethereal layer is separated and the aqueous layer re-extracted with ether. Evaporation of the combined, washed, and dried ethereal extracts under reduced pressure leaves the product as the residual solid, m.p. 72°-75.5° C. Recrystallization from hexane-cyclohexane affords purified material, m.p. 74°-75.5° C. A sample for analysis melts at 75°-76.5° C. after recrystallization from hexane.

Workup

  1. customflushed
  2. customreaction flask
  3. temperatureat reflux for 30 minutes
  4. stirringThe mixture is stirred at room temperature overnight
  5. customThe ethereal layer is separated
  6. extractionthe aqueous layer re-extracted with ether
  7. customEvaporation of the
  8. washwashed
  9. customdried ethereal extracts under reduced pressure
  10. customleaves the product as the residual solid, m.p. 72°-75.5° C
  11. customRecrystallization from hexane-cyclohexane
  12. customaffords
  13. custompurified material, m.p. 74°-75.5° C
  14. customA sample for analysis melts at 75°-76.5° C. after recrystallization from hexane

Sources & evidence

ORD record
ord-fd8477a6f893466782a275cdc75bf91e
Source dataset
uspto-grants-1976_10
Patent number
US03988454

Reaction notes

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