Ammonium Chloride → HCID 14834218, compound

HRID 477006Notes

Reaction equation

HRID 477006 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[CH:10]=[CH:11]/[C:12](OC)=[O:13].[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[CH:10]=[CH:11]/[CH2:12][OH:13]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 14834217HCID 14834217, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 14834218HCID 14834218, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 20 g of methyl (2E, 4E)-5-(2-chlorophenyl)-2,4-pentadienoate dissolved in 150 ml of toluene, 215 ml of diisobutylaluminum hydride (1.5M toluene solution) was added dropwise under ice-cooling over 1 hour. After stirring at the same temperature for 5 minutes, saturated aqueous ammonium chloride was slowly added, and the insolubles were filtered off. The filtrate was washed twice with saturated aqueous ammonium chloride, dried and then the solvent was distilled off to give 16.4 g of (2E, 4E)-5-(2-chlorophenyl)-2,4-pentadien-1-ol as an oily substance.

Workup

  1. temperaturecooling over 1 hour
  2. filtrationthe insolubles were filtered off
  3. washThe filtrate was washed twice with saturated aqueous ammonium chloride
  4. customdried
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-13a39cfadc384c77b90928f79d5cd49d
Source dataset
uspto-grants-1989_12
Patent number
US04886817

Reaction notes

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