HCID 88844966, compound → HCID 88846606, compound

HRID 1730089Notes

Reaction equation

HRID 1730089 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH2:6]/[C:7](/[CH3:22])=[CH:8]/[CH2:9][CH2:10]/[C:11](/[CH3:21])=[CH:12]/[CH2:13][CH:14](C(O)=O)[C:15]([OH:17])=[O:16])[CH3:3]>CCCCCCCCCC>[CH3:1][N:2]([CH2:4][CH2:5][CH2:6]/[C:7](/[CH3:22])=[CH:8]/[CH2:9][CH2:10]/[C:11](/[CH3:21])=[CH:12]/[CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH3:3]

Participants

3

Reactant 1

HCID 88844966HCID 88844966, compound

Product 1

HCID 88846606HCID 88846606, compoundYield 105.5%

Reagents, catalysts & solvents 1

HCID 15600DecaneSolvent

Procedure

To a boiling mixture of 6.2 g of sodium and 80 ml of xylene, with stirring are added gradually 80.2 g of geranylmalonic ester; the mixture is heated for one hour until all of the sodium is dissolved and then 29-32 g of dimethylaminoethyl chloride (in a solvent or without it) are added at a rate that ensures slight boiling of the reaction mixture. The reaction mixture is then heated with stirring so that the solvent boils until the reaction of a sample to phenolphthalein is neutral. After the mixture is cooled, the formed salt precipitate is dissolved by adding sufficient water, the reaction products are extracted with an organic solvent immiscible with water, for example with xylene. The solvent is then distilled and the residue (dimethylaminoethylgeranylmalonic ester) is fractionated in vacuum. As a result, 42 g of the dimethylaminoethylgeranylmalonic ester are produced. The boiling point of the ester is 178°-179° C/4 mm, n20 1.4720. To the boiling concentrated alcoholic solution of potassium hydroxide taken in excess, are added with stirring 42 g of dimethylaminoethylgeranylmalonic ester, the mixture is heated for one hour, then the alcohol is removed, the residue is dissolved in water and neutralized for example with hydrochloric acid. The isolated dimethylaminoethylgeranylmalonic acid is filtered with suction, washed with water and dried in a vacuum desiccator. As a result, 32 g of dimethylaminoethylgeranylmalonic acid are produced. The melting point of the acid is 145.5° - 146.0° C (with decomposition). The 32 g of dimethylaminoethylgeranylmalonic acid are decarboxylated in a hydrocarbon solvent having a boiling point of 150° C and above, for example in n-decane, after which the formed monocarboxylic acid is purified by fractionation in vacuum. 29 g of dimethylaminoethylgeranylacetic acid are obtained. The melting point of the acid is 183° - 185° C/2 mm, n20 1.4945.

Sources & evidence

ORD record
ord-85cdd3cd67384880bd72d6c23781d543
Source dataset
uspto-grants-1976_11
Patent number
US03991086

Reaction notes

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