Sodium Hydroxide → (2E)-3-(4-bromophenyl)prop-2-en-1-ol

HRID 1429262Notes

Reaction equation

HRID 1429262 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10](OCC)=[O:11])=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.[OH-].[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[CH2:10][OH:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 688115Ethyl trans-4-BromocinnamateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 11183465(2E)-3-(4-bromophenyl)prop-2-en-1-olYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-ethyl 3-(4-bromophenyl)acrylate (10.0 g, 39.2 mmol) in dichloromethane (151 mL) cooled to −78° C. was added a solution of diisobutylaluminum hydride (1.0 M in dichloromethane, 82 mL, 82 mmol) dropwise over 15 minutes time. The solution was then stirred for an additional 2 hours followed by the addition of a solution of 10% aqueous sodium hydroxide (250 mL). The mixture was allowed to warm to room temperature, and then the mixture was extracted with dichloromethane. The organic layer was dried and concentrated to afford 8.35 g (100%) of the title compound used directly in the next reaction.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. customThe organic layer was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1df2ed5218da463691bb152835a8ebce
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

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