Sodium Iodide → HCID 20267178, compound

HRID 1719562Notes

Reaction equation

HRID 1719562 reaction equation
O[CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]1[CH3:13].[I-].[Na+].[C-:16]#[N:17].[Na+]>CN(C)C=O>[CH3:13][CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:11][CH2:12][CH:3]1[CH2:2][C:16]#[N:17]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8929Sodium CyanideHCID 20267184HCID 20267184, compound

Product 1

HCID 20267178HCID 20267178, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 25.5 g of the p-toluenesulfonate ester of 2-hydroxymethyl-1-methyl-1,2,3,4-tetrahydronaphthalene, 2.25 g of sodium iodide and 7.5 g of sodium cyanide in 150 ml of dimethylformamide was stirred for about 20 hours at room temperature. The reaction mixture was poured into ice and extracted with ether. The extracts were dried over anhydrous magnesium sulfate and concentrated to a brown oil (15.2 g). The latter was treated with pentane to afford 12.5 g of 1,2,3,4-tetrahydro-1-methyl-2-naphthaleneacetonitrile as a colorless solid which melted at room temperature.

Workup

  1. additionThe reaction mixture was poured into ice
  2. extractionextracted with ether
  3. dry with materialThe extracts were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated to a brown oil (15.2 g)
  5. additionThe latter was treated with pentane

Sources & evidence

ORD record
ord-2279fb50cbae4e5fba0408211749f154
Source dataset
uspto-grants-1985_09
Patent number
US04540705

Reaction notes

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