Ethyl diazoacetate → 3-(4-Chlorophenoxy)-2,2-dimethylcyclopropanecarboxylic acid

HRID 2049822Notes

Reaction equation

HRID 2049822 reaction equation
ClC1C=CC(OC=C(C)C)=CC=1.[N+](=CC(OCC)=O)=[N-].[Cl:21][C:22]1[CH:38]=[CH:37][C:25]([O:26][CH:27]2[CH:29]([C:30]([O:32]CC)=[O:31])[C:28]2([CH3:36])[CH3:35])=[CH:24][CH:23]=1>[Cu]>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([O:26][CH:27]2[CH:29]([C:30]([OH:32])=[O:31])[C:28]2([CH3:35])[CH3:36])=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 12192Ethyl diazoacetateHCID 20344552Ethyl 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylateHCID 20344578HCID 20344578, compound

Product 1

HCID 203049613-(4-Chlorophenoxy)-2,2-dimethylcyclopropanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

Following the procedure of Example 1B, 7.2 g (0.040 mol) of 3-(4-chlorophenoxy)-2-methyl-2-propene and 0.2 g copper powder are reacted with 8.7 g (0.079 mol) ethyl diazoacetate to yeild ethyl 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylate, which is then hydrolyzed to give 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylic acid.

Sources & evidence

ORD record
ord-6126c7b4137145c1bae69f176c16d211
Source dataset
uspto-grants-1980_04
Patent number
US04198527

Reaction notes

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