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Gamma-undecalactone → 4-Hydroxy-undecanoic acid dodecylamide

HRID 2304955
Notes
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Reaction equation

HRID 2304955 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[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>C(Cl)Cl>[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

HCID 539853184-Hydroxy-undecanoic acid dodecylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 19.0 g aluminum chloride, dissolved in methylene chloride, was cooled to 0° C. and 46.5 g dodecylamine in methylene chloride was added dropwise (exothermic). At room temperature, 19.3 g gamma-undecalactone was added rapidly. The temperature rose to 36° C. The reaction was stirred at room temperature for 4 hours. The mixture was quenched with water and filtered over Celite. The liquid was extracted with ether and washed with water and brine. The solution was dried, filtered and evaporated to dryness. The resulting brown crystals were purified by recrystallization from ether/ethylacetate to give pale yellow crystals.

Workup

  1. customrose to 36° C
  2. customThe mixture was quenched with water
  3. filtrationfiltered over Celite
  4. extractionThe liquid was extracted with ether
  5. washwashed with water and brine
  6. customThe solution was dried
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe resulting brown crystals were purified by recrystallization from ether/ethylacetate
  10. customto give pale yellow crystals

Sources & evidence

ORD record
ord-491a19afb3174b878e9a949db83ba780
Source dataset
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06437150B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes