Azelaic Acid → HCID 11156309, compound

HRID 1866488Notes

Reaction equation

HRID 1866488 reaction equation
[C:1]([O-:4])([O-:3])=O.[Cs+].[Cs+].[Na+].[I-].[C:9]([OH:21])(=[O:20])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=O.[C:22]([O:31][CH2:32]Cl)(=[O:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].[CH2:34]1[CH2:38][O:37][CH2:36][CH2:35]1>>[C:17]([O:3][CH2:1][O:4][C:36](=[O:37])[CH2:35][CH2:34][CH2:38][CH2:9][CH2:10][CH2:11][CH3:12])(=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]([O:21][CH2:32][O:31][C:22](=[O:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:20]

Participants

6

Reactant 5

HCID 2266Azelaic AcidHCID 5238Sodium IodideHCID 8028Tetrahydrofuran2×HCID 10796Cesium carbonateHCID 525231Chloromethyl octanoate

Product 1

HCID 11156309HCID 11156309, compoundYield 47.9%

Conditions

Temperature
60 °C

Procedure

A heterogeneous solution of Cs2CO3 (2.60 g, 4.00 mmol), NaI (30 mg, 0.20 mmol) and nonanedioic acid (0.75 g, 4.00 mmol) in THF (20 ml) was stirred for ½ hour at 60° C. Chloromethyl octanoate (1.53 g, 8.00 mmol) in THF (5 ml) was added dropwise added to the solution and stirred at 60° C. for 48 hours. The reaction mixture was cooled to room temperature and evaporated in vacuo. Diethyl ether (20 ml) was added and the residue was washed with saturated NaHCO3 (3×15 ml), dried with MgSO4 and filtered. Evaporation in vacuo gave the product as a colourless oil (0,95 g, 47.9%). 1H-NMR (CDCl3) δ 5.76 (s, 4H), 2.37 (t, 8H), 1.65 (t, 8H), 1.30 (s br, 22H), 90 (t, 6H). 13C-NMR (CDCl3) δ 172.89, 62.32, 79.44, 34.35, 34.26, 31.99, 29.32, 29.23, 29.14, 24.99, 24.86, 22.94, 14.41.

Workup

  1. additionadded to the solution
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customevaporated in vacuo
  4. additionDiethyl ether (20 ml) was added
  5. washthe residue was washed with saturated NaHCO3 (3×15 ml)
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. customEvaporation in vacuo

Sources & evidence

ORD record
ord-3fea7667274348ed9a808f3d48c4ed57
Source dataset
uspto-grants-2009_12
Patent number
US07629383B2

Reaction notes

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