1-Dodecanol → HCID 10428617, compound

HRID 728689Notes

Reaction equation

HRID 728689 reaction equation
C1[O:6][C:5]([CH2:11][C:12]([OH:14])=[O:13])([CH2:7][C:8]([OH:10])=[O:9])[C:3](=[O:4])[O:2]1.C(N(CC)CC)C.[CH2:22](O)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>C(O)C>[CH2:33]([CH:7]([C:5]([CH2:11][C:12]([OH:14])=[O:13])([C:3]([OH:2])=[O:4])[OH:6])[C:8]([OH:10])=[O:9])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH3:22]

Participants

5

Reactant 3

HCID 81931-DodecanolHCID 8471TriethylamineHCID 8945Anhydromethylenecitric acid

Product 1

HCID 10428617HCID 10428617, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2 (10 g), triethylamine (15 ml) and dodecanol (22 ml) in ethanol-free chloroform (100 ml) was refluxed for 22 hours. Workup in the usual fashion gave the crude product (15.3 g, 86%) as a semi-solid. GC analysis indicated the mixture contained an 89:6 mixture of the major and minor isomers together with about 4% of unreacted 2. Crystallization of this material gave 11.8 g of 3c with mp 74.8°-75.6° C. Recrystallization gave 3c with mp 74.7°-75.3° C., which migrated as a single spot on TLC and as a broad peak, Rt 10.88-10.93, by GC, after derivatization.

Workup

  1. temperaturewas refluxed for 22 hours
  2. customWorkup in the usual fashion gave the crude product (15.3 g, 86%) as a semi-solid
  3. additionan 89:6 mixture of the major and minor isomers together with about 4% of unreacted 2
  4. customCrystallization of this material

Sources & evidence

ORD record
ord-595cbce8dcd04f0abab55f44e8fbe2c3
Source dataset
uspto-grants-1991_09
Patent number
US05049699

Reaction notes

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