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

HRID 1076567Notes

Reaction equation

HRID 1076567 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 three hours and then heated under reflux for about five 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 five 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-4bd4e5883c5c43638c896fc8a182dcf0
Source dataset
uspto-grants-1976_05
Patent number
US03957787

Reaction notes

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