Ammonium Chloride → HCID 10679056, compound

HRID 2229225Notes

Reaction equation

HRID 2229225 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][C:12]=1/[CH:21]=[CH:22]/[C:23](OC)=[O:24].[NH4+].[Cl-]>C1(C)C=CC=CC=1.C(Cl)Cl>[CH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][C:12]=1/[CH:21]=[CH:22]/[CH2:23][OH:24]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 816753HCID 816753, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 10679056HCID 10679056, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of diisobutylaluminum hydride in toluene (1.5M, 18 ml) was added dropwise to a solution of methyl (E)-3-(2-naphthyl)-acrylate (2.52 g) in CH2Cl2 at −78 ° C. and the mixture was stirred at −78° C. for 1 hour. Saturated aqueous solution of NH4Cl was added to the mixture and organic layer was washed with 1N HCl and brine, dried and concentrated. The residue was crystallized from CH2Cl2-hexane to give the titled compound (1.78 g) as a white solid.

Workup

  1. washwas washed with 1N HCl and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was crystallized from CH2Cl2-hexane

Sources & evidence

ORD record
ord-676aaee296f240b4959e31399ebd2b1b
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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