Acetic Acid → HCID 86737823, compound

HRID 1680858Notes

Reaction equation

HRID 1680858 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]=[O:14])[CH:7]=[CH:6]2.[C-:15]#[N:16].[Na+].C(O)(=O)C.O>C(O)C>[C:15]([C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH:6]=[CH:7][C:8]=1[CH2:13][OH:14])#[N:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 8929Sodium CyanideHCID 769916-Methoxy-2-naphthaldehyde

Product 1

HCID 86737823HCID 86737823, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.5 g of 6-methoxy-2-naphthaldehyde are treated with a solution of 4.28 g of sodium cyanide in 115 ml of 95% ethanol. 11.5 ml of acetic acid are then added dropwise at 0° C. over a period of 1 hour. The mixture is left to react overnight and then 400 ml of water are needed. The mixture is extracted three times with ether, the ether extracts are washed with 10% potassium bicarbonate solution and semisaturated and saturated sodium chloride solution. The extracts are dried over sodium sulfate and evaporated to yield α-cyano-(6-methoxy-2-naphthyl)methanol which, without further purification, is reacted with cyclopropane carboxylic acid chloride in the process of Example 2. The resulting product is cyclopropane carboxylic acid α-cyano-(6-methoxy-2-naphthyl)methyl ester; nD20 =1.5765.

Workup

  1. waitThe mixture is left
  2. customto react overnight
  3. extractionThe mixture is extracted three times with ether
  4. washthe ether extracts are washed with 10% potassium bicarbonate solution
  5. dry with materialThe extracts are dried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-e01750c1517342be89f1060fa734eca0
Source dataset
uspto-grants-1981_06
Patent number
US04276305

Reaction notes

Loading…