Ammonium Chloride → (2E)-3-(2-Naphthalenyl)-2-buten-1-ol

HRID 2229226Notes

Reaction equation

HRID 2229226 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/[C:21](/[CH3:27])=[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/[C:21](/[CH3:27])=[CH:22]/[CH2:23][OH:24]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 15933618HCID 15933618, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 69946163(2E)-3-(2-Naphthalenyl)-2-buten-1-olYield 98%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of diisobutylaluminum hydride in toluene (1.5M, 45 ml) was added dropwise to a solution of methyl (E)-3-(2-naphthyl)crotonate (6.01 g) in CH2Cl2 at −78° C. and the mixture was stirred at −78° C. for 4 hours. 1N-Hhydrochloric acid and saturated aqueous solution of NH4Cl were added to the mixture and organic layer was washed with 1N HCl and brine, dried and concentrated. The residue was crystallized from hexane to give the titled compound (5.16 g) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-6567521f93894ab88d91fae6e07228b6
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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