Methanol → 39739-56-5

HRID 2232058Notes

Reaction equation

HRID 2232058 reaction equation
[C:1]1([CH2:11][C:12]#[N:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.CO.[C:16]([Cl:19])(=[O:18])C>CCOCC>[ClH:19].[CH3:16][O:18][C:12](=[NH:13])[CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6367Acetyl chlorideHCID 85961-Naphthaleneacetonitrile

Product 1

HCID 1986396439739-56-5Yield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred mixture of 1-naphthylacetonitrile (9.2 g, 0.055 mol), methanol (5.0 mL, 0.124 mol), and ether (5 mL) was added acetyl chloride (5.2 g, 0.066 mol) dropwise. Stirring was continued for 30 minutes and the mixture was allowed to stand at room temperature for 60 hours. The resulting precipitate was collected by filtration, washed with ether, crushed with a mortar and pestle, and again washed with ether. The product was dried in vacuo to give a white crystalline solid (11.7 g, 91%), which was used without further purification.

Workup

  1. stirringStirring
  2. waitto stand at room temperature for 60 hours
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with ether
  5. customcrushed with a mortar and pestle
  6. washagain washed with ether
  7. customThe product was dried in vacuo

Sources & evidence

ORD record
ord-728227c0d99147e0a37f1d7ea3fa1963
Source dataset
uspto-grants-1988_11
Patent number
US04786640

Reaction notes

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