Methyl iodide → HCID 21412528, compound

HRID 2072565Notes

Reaction equation

HRID 2072565 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:5]2.[H-].[Na+].[CH3:19]OCCOC.CI>C(O)C.O>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH:12]([CH3:19])[C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:5]2

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 80711,2-DimethoxyethaneHCID 24758Sodium hydrideHCID 20335017HCID 20335017, compound

Product 1

HCID 21412528HCID 21412528, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 22 g. of methyl 6-methyl-2-naphthylacetate, 2.5 g. of sodium hydride and 150 ml. of 1,2-dimethoxyethane, 25 g. of methyliodide are added. The reaction mixture is allowed to stand for several hours; then it is diluted with ethanol followed by water and extracted with methylene chloride. The extracts are combined, washed with water to neutrality, dried over sodium sulfate, filtered, and evaporated to yield methyl 6-methyl-2-naphthyl-α-methylacetate. This derivative is hydrolyzed by means of the process described in Part H of Example 2 to obtain 6-methyl-2-naphthyl-α-methylacetic acid.

Workup

  1. additionTo a mixture of 22 g
  2. waitto stand for several hours
  3. extractionextracted with methylene chloride
  4. washwashed with water to neutrality
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-e52411fdb24649a588d9c4fbece6584c
Source dataset
uspto-grants-1977_09
Patent number
US04051233

Reaction notes

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