Hydrochloric Acid → 2-(2-Bromophenyl)ethan-1-ol

HRID 1414211Notes

Reaction equation

HRID 1414211 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][C:15](OCC)=[O:16].O.Cl>CCOCC>[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][OH:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2780092Ethyl 2-(2-bromophenyl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 27340892-(2-Bromophenyl)ethan-1-olYield 85.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred suspension of 106.0 g of lithium aluminum hydride in 3.7 l of anhydrous ether, is added, dropwise, a solution of 780.0 g of ethyl o-bromophenylacetate in 3.1 l of anhydrous ether. The reaction mixture is stirred for about 3 hours and then heated under reflux for about 5 hours. The mixture is cooled, then treated dropwise with 800 ml of water, and 1.5 l of 10% aqueous hydrochloric acid. The ether solution is washed, dried, concentrated, and the residue is distilled to give 554.0 g of o-bromophenethyl alcohol, bp. about 130°-132° (8mm), nD20 1,5760.

Workup

  1. additionis added
  2. temperatureheated
  3. temperatureunder reflux for about 5 hours
  4. temperatureThe mixture is cooled
  5. washThe ether solution is washed
  6. customdried
  7. concentrationconcentrated
  8. distillationthe residue is distilled

Sources & evidence

ORD record
ord-6bae72c136d0493ab258c88403524551
Source dataset
uspto-grants-1977_01
Patent number
US04001233

Reaction notes

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