Gamma-undecalactone → 4-Hydroxy-undecanoic acid dodecylamide

HRID 841155Notes

Reaction equation

HRID 841155 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[CH2:5]([NH2:17])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH3:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]1[O:30][C:28](=[O:29])[CH2:27][CH2:26]1>ClCCl>[CH2:5]([NH:17][C:28](=[O:29])[CH2:27][CH2:26][CH:25]([OH:30])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH3:18])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 7714Gamma-undecalactoneHCID 13583DodecylamineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 539853184-Hydroxy-undecanoic acid dodecylamideYield 6.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of 19.0 g aluminum trichloride in 50 ml of dichloromethane, a solution of 46.5 g dodecylamine in 50 ml of dichloromethane was dropped in at 15-20° C. Then 19.3 g gamma-undecalactone were added quickly at room temperature and an additional 50 ml of dichloromethane was added. After 4 hours, the reaction mixture was quenched with water and filtered through celite. The filtrate was diluted with ether and washed with brine. The organic phase was dried, filtered and evaporated to dryness. The resulting brown solid was purified by recrystallisation to yield 2.65 g of colourless crystals.

Workup

  1. customthe reaction mixture was quenched with water
  2. filtrationfiltered through celite
  3. additionThe filtrate was diluted with ether
  4. washwashed with brine
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe resulting brown solid was purified by recrystallisation

Sources & evidence

ORD record
ord-15f10c7439844911ab977e3fa5c6c16f
Source dataset
uspto-grants-2002_04
Patent number
US06369248B1

Reaction notes

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