Methanol → HCID 21845407, compound

HRID 619008Notes

Reaction equation

HRID 619008 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][N:5]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C[O-].[Na+].[CH3:26][C:27](=[CH:29][CH2:30][CH2:31]/[C:32](=[CH:34]/CO)/[CH3:33])[CH3:28].CO>C1(C)C=CC=CC=1>[CH2:1]([O:2][C:3](=[O:22])[CH2:4][N:5]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])/[CH:26]=[C:27](/[CH2:29][CH2:30][CH:31]=[C:32]([CH3:34])[CH3:33])\[CH3:28]

Participants

6

Reactant 4

HCID 887MethanolHCID 637566GeraniolHCID 10942334Sodium MethoxideHCID 21845428HCID 21845428, compound

Product 1

HCID 21845407HCID 21845407, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of N,N-dioctylglycine methyl ester (47.02 g, 150 mmol, 1 eq) in toluene (250 ml) under argon was slowly added some sodium methoxide (1.01 g, 0.019 mol, 0.125 eq) and geraniol (27.3 ml, 158 mmol, 1.05 eq). The mixture was heated under vacuum (10 mm Hg) and the methanol produced by the transesterification reaction is distilled with toluene over one hour after which the reaction appeared completed by 1H NMR. Any remaining toluene is evaporated under vacuum. Diethyl ether was added (200 ml) and the mixture stored at 4° C. for one hour prior to filtration. The filtrate was then concentrated under vacuum yielding to the expected N,N-dioctylglycine geranyl ester as a light yellow oil (quantitative yield).

Workup

  1. temperatureThe mixture was heated under vacuum (10 mm Hg)
  2. distillationis distilled with toluene over one hour after which the reaction
  3. customAny remaining toluene is evaporated under vacuum
  4. additionDiethyl ether was added (200 ml)
  5. filtrationto filtration
  6. concentrationThe filtrate was then concentrated under vacuum

Sources & evidence

ORD record
ord-322237a9f30a46cc93b9ecfb3cfc2f62
Source dataset
uspto-grants-1999_09
Patent number
US05958870

Reaction notes

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