Hydrazine hydrate (1:1) → 8-(2,4-Dimethylphenyl)-octanoic acid ethyl ester

HRID 1156179Notes

Reaction equation

HRID 1156179 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](=O)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=1[CH3:19])[CH3:2].O.NN>C(O)COCCO.C(O)C.S(=O)(=O)(O)O>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=1[CH3:19])[CH3:2]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 543546598-(2,4-Dimethylphenyl)-7-oxo-octanoic acid ethyl ester

Product 1

HCID 542283578-(2,4-Dimethylphenyl)-octanoic acid ethyl esterYield 61.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1118Sulfuric AcidSolventHCID 8117Diethylene GlycolSolvent

Procedure

12.8 g of 8-(2,4-dimethylphenyl)-7-oxo-octanoic acid ethyl ester [obtained according to (d)] are reduced, analogously to the method described by Huisgen [R. Huisgen et al., Liebigs Ann. 586 (1954), 52] with hydrazine hydrate in diethylene glycol. The isolated reduction product, in 200 ml of ethanol and 5 ml of concentrated sulphuric acid, is heated at the reflux temperature overnight and, after customary working up, gives 7.5 g of 8-(2,4-dimethylphenyl)-octanoic acid ethyl ester as a colourless oil.

Sources & evidence

ORD record
ord-af1430bf36104d9297c2c15ae6f9a678
Source dataset
uspto-grants-1982_06
Patent number
US04334089

Reaction notes

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