ChemicalBook CAS DataBase List GERANIC ACID

GERANIC ACID synthesis

7synthesis methods

Product Name:GERANIC ACID
CAS Number:459-80-3
Molecular formula:C10H16O2
Molecular Weight:168.23

Geranic acidacid is produced
1) from 2-Methylhepten-2-one-6 with Iodoor Bromoacetic ester and a Zinc type catalyst.
2) by oxidation of Citral.

502-65-8 Synthesis

502-65-8
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459-80-3
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Yield:459-80-3 1.036 g

Reaction Conditions:

with oxygen in ethyl acetate at 68; for 21 h;

Steps:

Preparation of O Lyc
Lycopene (817 mg) was placed in a 3-neck flask with stir bar, reflux condenser and 0₂ inlet (Pasteur pipette). Ethyl acetate (20.4 mL) was added, 0₂ was bubbled through and the stirred mixture was lowered into an oil bath at 68°C. After 21 h, the reaction was stopped and the slightly cloudy yellow liquid was cooled to room temp. The absorbance of a filtered sample was measured as 0.272 at 380 nm in a 1 cm cuvette at ca. 1.0 g/L. The cloudy yellow liquid was centrifuged, the supernatant decanted and the solid residue rinsed/centrifuged with ethyl acetate (2 3 mL), decanting the supernatant each time. The solid residue was dried under vacuum for 4 h to give a pale yellow, flaky solid (38 mg). The combined supernatant liquids were transferred to a 50 mL round bottom flask and solvent was removed on the rotary- evaporator at 40 °C down to a pressure of 30 mm Hg. The residue was transferred to a vacuum pump and dried for 4 h to give a foam-like, yellow solid (1.036 g) as OxLyc.

References:

AVIVAGEN INC.;BURTON, Graham, W.;DAROSZEWSKI, Janusz;MOGG, Trevor, J.;NIKIFOROV, Grigory, B.;NICKERSON, James, G.;GROOME, Cameron, L. WO2017/143460, 2017, A1 Location in patent:Paragraph 00107

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