Water → 2-(3-Bromophenyl)ethan-1-ol

HRID 2117956Notes

Reaction equation

HRID 2117956 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:9]=[C:10]([CH2:14][C:15](O)=[O:16])[CH:11]=[CH:12][CH:13]=1.O.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>O1CCCC1>[Br:7][C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][OH:16])[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9357Potassium Sodium TartrateHCID 74653(3-Bromophenyl)acetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 27340902-(3-Bromophenyl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminium hydride in dry tetrahydrofuran (50 ml) was added (3-bromophenyl)acetic acid (10 g) in tetrahydrofuran (100 ml) under ice cooling. The mixture was refluxed for 2 hurs. After cooling, to the reaction mixture were added water and aqueous Rochelle salt. The mixture was stirred for another 30 min. Aqueous layer was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo to give 2-(3-bromophenyl)ethanol. This compound was used for the next reaction without further purification.

Workup

  1. temperatureThe mixture was refluxed for 2 hurs
  2. temperatureAfter cooling, to the reaction mixture
  3. extractionAqueous layer was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ed01c1f40fd5494eafb9f4ec23790caa
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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