m-Chlorophenylacetonitrile → Ethyl 6-(3'chlorophenyl)-6-cyano-5-keto-3,3-dimethylhexanoate

HRID 370387

Reaction equation

HRID 370387 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][C:6]#[N:7].[CH3:11][C:12]([CH3:25])([CH2:19][C:20](OCC)=[O:21])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].[Na]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]([C:6]#[N:7])[C:20](=[O:21])[CH2:19][C:12]([CH3:25])([CH3:11])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 73722m-ChlorophenylacetonitrileHCID 87314Pentanedioic acid, 3,3-dimethyl-, 1,5-diethyl esterHCID 5360545Sodium

Product 1

HCID 20275820Ethyl 6-(3'chlorophenyl)-6-cyano-5-keto-3,3-dimethylhexanoateYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Starting with 75.0 g (0.495 mol) of 3-chlorobenzyl cyanide, 160.58 g (0.743 mol) of diethyl 3,3-dimethylglutarate, 14.80 g (0.643 mol) of sodium, and 260 ml of dry ethanol a total of 108.08 g (71% yield) of the desired product was obtained using the procedure described in Example I, Part A.

Sources & evidence

ORD record
ord-4e9e4c131d5b4a46bf20b2e5f5c0468f
Source dataset
uspto-grants-1985_07
Patent number
US04526723

Linked notes

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