Diazomethane → HCID 21412550, compound

HRID 1576467Notes

Reaction equation

HRID 1576467 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])[CH:8]=[CH:7]2)(=[O:3])[CH3:2].[N+](=[CH2:21])=[N-]>C(OCC)C>[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([CH:14]([CH3:18])[C:15]([O:17][CH3:21])=[O:16])[CH:8]=[CH:7]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 20334987HCID 20334987, compound

Product 1

HCID 21412550HCID 21412550, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of 24 g. of 6-acetyl-2-naphthyl-α-methylacetic acid and 200 ml. of diethyl ether are added 4.2 g. of diazomethane in 100 ml. of diethyl ether. The resulting mixture is evaporated to give methyl 6-acetyl-2-naphthyl-α-methylacetate. The product is added to 200 ml. of aqueous 20% sodium hypochlorite. The resulting mixture is allowed to stand for 4 hours at room temperature. The mixture is acidified by the addition of aqueous 1N hydrochloric acid and extracted with diethyl ether. The extracts are combined, washed with water to neutrality, dried over sodium sulfate, filtered, evaporated to give 6-carboxy-2-naphthyl-α-methylacetic acid.

Workup

  1. additionTo a mixture of 24 g
  2. customThe resulting mixture is evaporated

Sources & evidence

ORD record
ord-21719a5988774f83902336bf8e47310b
Source dataset
uspto-grants-1976_09
Patent number
US03980699

Reaction notes

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