Methanol → HCID 20518065, compound

HRID 2198681Notes

Reaction equation

HRID 2198681 reaction equation
[NH2:1][CH:2]([CH2:17][CH3:18])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=[O:13].S(=O)(=O)(O)O.[CH3:24]O>>[CH3:24][O:13][C:12](=[O:14])[C:11]([CH3:15])([CH3:16])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]([NH2:1])[CH2:17][CH3:18]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 20518072HCID 20518072, compound

Product 1

HCID 20518065HCID 20518065, compoundYield 89.5%

Procedure

51.4 g (0.2 mole) of 11-amino-2,2-dimethyl-tridecanoic acid and 200 ml of methanol and 22 g (0.224 mole) of sulfuric acid are refluxed for 3 hours. Excess methanol is then distilled off, the residue is diluted with about 200 ml of water and the reaction solution is made weakly alkaline (pH 8-10) with aqueous sodium hydroxide, whereupon the aminoacid ester separates as upper organic phase. Subsequent distillation yields 48.5 g (0.179 mole) of 11-amino-2-,2-dimethyl-tridecanoic acid methyl ester, corresponding to a yield of 89.5% of theory.

Workup

  1. distillationExcess methanol is then distilled off
  2. additionthe residue is diluted with about 200 ml of water
  3. distillationSubsequent distillation

Sources & evidence

ORD record
ord-9dd0a43fb7fe44249026da7ce32a68bf
Source dataset
uspto-grants-1982_11
Patent number
US04359418

Reaction notes

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