Methanol → HCID 10918868, compound

HRID 619010Notes

Reaction equation

HRID 619010 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][N:5]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:6][C:7]([O:9][CH3:10])=[O:8].C[O-].[Na+].[CH3:27][C:28](=[CH:30][CH2:31][CH2:32]/[C:33](=[CH:35]/CO)/[CH3:34])[CH3:29].CO>C1(C)C=CC=CC=1>[CH2:10]([O:9][C:7](=[O:8])[CH2:6][N:5]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:4][C:3]([O:2][CH2:1]/[CH:35]=[C:33](/[CH2:32][CH2:31][CH:30]=[C:28]([CH3:27])[CH3:29])\[CH3:34])=[O:23])/[CH:27]=[C:28](/[CH2:30][CH2:31][CH:32]=[C:33]([CH3:35])[CH3:34])\[CH3:29]

Participants

6

Reactant 4

HCID 887MethanolHCID 637566GeraniolHCID 10942334Sodium MethoxideHCID 21845391HCID 21845391, compound

Product 1

HCID 10918868HCID 10918868, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of N-dodecyl-N-(2-methoxy-2-oxoethyl)glycine methyl ester (6.59 g, 20 mmol, 1 eq) in toluene (80 ml) under argon was slowly added some sodium methoxide (0.27 g, 0.005 mol, 2*0.125 eq) and geraniol (7.3 ml, 42 mmol, 2*1.05 eq). The mixture was heated under vacuum (10 mm Hg) and the methanol produced by the transesterification reaction was distilled with toluene over two hours after which the reaction appeared completed by 1H NMR. Any remaining toluene was 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-dodecyl-N-(2-geranyloxy-2-oxoethyl)glycine geranyl ester as a light brown oil (quantitative yield).

Workup

  1. temperatureThe mixture was heated under vacuum (10 mm Hg)
  2. distillationwas distilled with toluene over two hours after which the reaction
  3. customAny remaining toluene was 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-7c890540588f4724b66f9a5df8e64a35
Source dataset
uspto-grants-1999_09
Patent number
US05958870

Reaction notes

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