Hydrochloric Acid → 2.2-Dihexadecylmalonic acid dihexadecyl ester

HRID 650458Notes

Reaction equation

HRID 650458 reaction equation
[H-].[Na+].[CH2:3]([O:19][C:20](=[O:57])[CH:21]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].I[CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH3:74].Cl>O1CCCC1.CN(C)C=O.O>[CH2:3]([O:19][C:20](=[O:57])[C:21]([CH2:74][CH2:73][CH2:72][CH2:71][CH2:70][CH2:69][CH2:68][CH2:67][CH2:66][CH2:65][CH2:64][CH2:63][CH2:62][CH2:61][CH2:60][CH3:59])([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 110071-IodohexadecaneHCID 24758Sodium hydrideHCID 539711392-Hexadecylmalonic acid dihexadecyl ester

Product 1

HCID 543016182.2-Dihexadecylmalonic acid dihexadecyl esterYield 66%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (72 mg, 3 mmol) was added in portions to a cooled (ice/water) solution of 2-hexadecylmalonic acid dihexadecyl ester (2.33 g, 3 mmol) in tetrahydrofuran (45 ml) under an argon atmosphere and the resulting mixture was stirred at ambient temperature for 30 minutes. The solvent was evaporated and the solid residue was redissolved in N,N-dimethylformamide (45 ml). A solution of 1-iodohexadecane (1.06 g, 3 mmol) in N,N-dimethylformamide (20 ml) was added and stirring was continued at room temperature for 24 hours. Water (75 ml) was added to the reaction mixture after the pH had been adjusted to about 5 with 2N HCl. The mixture was extracted with chloroform (3×75 ml) and the chloroform phase was washed with water (3×75 ml). The organic phase was dried with magnesium sulphate and the solvent was removed at reduced pressure. The residue was purified by flash chromatography (silicagel 60, chloroform/hexane). Yield: 66%. 1H-NMR (300 MHz, CDCl3): δ 0.88(t,12H), 1.26(m,108H), 1.60(m,4H), 1.85(m,4H), 4.09(t,4H). FAB-MS: 1024 (M+Na).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe solid residue was redissolved in N,N-dimethylformamide (45 ml)
  3. stirringstirring
  4. waitwas continued at room temperature for 24 hours
  5. extractionThe mixture was extracted with chloroform (3×75 ml)
  6. washthe chloroform phase was washed with water (3×75 ml)
  7. dry with materialThe organic phase was dried with magnesium sulphate
  8. customthe solvent was removed at reduced pressure
  9. customThe residue was purified by flash chromatography (silicagel 60, chloroform/hexane)

Sources & evidence

ORD record
ord-f46d6485b5a1461ba540f676f80ef796
Source dataset
uspto-grants-2001_08
Patent number
US06274120B1

Reaction notes

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