Methanol → 5,6-Dimethoxy-1,2,3,4-tetrahydronaphthalene-1,2-dicarbonitrile

HRID 2290904Notes

Reaction equation

HRID 2290904 reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[C:8]([O:15][CH3:16])[C:9]([O:13][CH3:14])=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH:4]=1)#[N:2].CO.C(OCC)C.[C-:24]#[N:25].[K+]>O>[C:1]([CH:3]1[C:12]2[C:7](=[C:8]([O:15][CH3:16])[C:9]([O:13][CH3:14])=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH:4]1[C:24]#[N:25])#[N:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 9032Potassium CyanideHCID 135385495,6-Dimethoxy-3,4-dihydronaphthalene-1-carbonitrile

Product 1

HCID 137460035,6-Dimethoxy-1,2,3,4-tetrahydronaphthalene-1,2-dicarbonitrileYield 41.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A suspension of the compound of example 1 (29.2 g, 0.14 mole), 315 mL MeOH, and 110 mL diethyl ether was stirred mechanically, just below reflux temperature as a 45° solution of KCN (34 g, 0.52 mole) in 94 mL water was added dropwise, quickly. The reaction mixture was stirred at reflux for 1.5 hr. After cooling briefly a solution of NH4OAc (21 g, 0.27 mole) in 34 mL water was added. Water was added until cloudy and the solution was stored at 0° for 2 days. The solid was filtered, washed with 60° water, cold 50% aqueous MeOH, and dried (high-vacuum) to yield 14.0 g tan solid (41%); mp 107°-8°; M+ 242.

Workup

  1. additionwas added dropwise
  2. stirringThe reaction mixture was stirred
  3. temperatureat reflux for 1.5 hr
  4. additionwas added
  5. filtrationThe solid was filtered
  6. washwashed with 60° water, cold 50% aqueous MeOH
  7. customdried (high-vacuum)

Sources & evidence

ORD record
ord-a60d00308b9b430ca8733927d1a7d19e
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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