Water → HCID 11032969, compound

HRID 1788884Notes

Reaction equation

HRID 1788884 reaction equation
O.[CH2:2]([NH2:11])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:12]([CH2:16][CH2:17][CH2:18][CH2:19][C:20](Cl)=[O:21])([O:14]C)=[O:13].[OH-].[Na+]>CCOCC>[CH2:2]([NH:11][C:20](=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][C:12]([OH:14])=[O:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 16215NonylamineHCID 520737Methyl 6-chloro-6-oxohexanoate

Product 1

HCID 11032969HCID 11032969, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A two liter beaker fitted with a mechanical stirrer, ice bath, and pH electrode, was charged with 700 mL of water and 89.4 g (0.624 mol) of nonylamine in 200 mL of ether. To this stirred mixture was added dropwise over a 30 minute period a solution of the above 5-carbomethoxyvaleryl chloride in 100 mL of ether. Concurrent with addition of the ether solution was added 50% sodium hydroxide solution at a rate such as to keep the pH of the aqueous layer between 10 and 12. Following addition of the acid chloride and sodium hydroxide the reaction mixture was added to a two L separatory funnel and extracted with 300 mL methylene chloride. The methylene chloride layer was separated, washed with 300 mL saturated sodium chloride solution, and dried over magnesium sulfate. Removal of the methylene chloride on a rotary evaporator yielded a yellow oil which solidified upon standing. Recrystallization from hexane afforded the methylester of 6-nonylamino-6-oxocaproic acid as colorless crystals, mp 56°-57° C., weight 155.1 g. Upon cooling to -15° C. the filtrate deposited an additional 11.0 of product. Total yield was 166.1 g (93%).

Workup

  1. customA two liter beaker fitted with a mechanical stirrer, ice bath
  2. additionwas added to a two L separatory funnel
  3. extractionextracted with 300 mL methylene chloride
  4. customThe methylene chloride layer was separated
  5. washwashed with 300 mL saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customRemoval of the methylene chloride
  8. customon a rotary evaporator
  9. customyielded a yellow oil which
  10. customRecrystallization from hexane

Sources & evidence

ORD record
ord-db3f623b9a90456fae3c2ef1e6893c91
Source dataset
uspto-grants-1987_08
Patent number
US04686063

Reaction notes

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