Phenacyl bromide → Phenacyl 3-hydroxy-2-n-tetradecyl-11-icosenoate

HRID 728749Notes

Reaction equation

HRID 728749 reaction equation
[OH:1][CH:2]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[CH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:4]([OH:6])=[O:5].[CH2:38](Br)[C:39]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:40].C(N(CC)CC)C>O1CCCC1>[OH:1][CH:2]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[CH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:4]([O:6][CH2:38][C:39]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:40])=[O:5]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 8471TriethylamineHCID 539401263-Hydroxy-2-n-tetradecyl-11-icosenoic acid

Product 1

HCID 53739963Phenacyl 3-hydroxy-2-n-tetradecyl-11-icosenoateYield 22.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Hydroxy-2-n-tetradecyl-11-icosenoic acid (II)(3.68 g, 7.04 millimole) was dissolved in dry tetrahydrofuran (100 ml), and phenacyl bromide (2.10 g, 10.56 millimole) and triethyl amine (1.47 ml, 10.56 millimole) were successively added thereto with ice cooling. The reaction mixture was allowed to warm to room temperature, and to react for 13.5 hours. The insoluble matter in the reaction mixture was filtered off with suction and the solvent was distilled off from the filtrate. The residue was dissolved in methylene chloride and the obtained solution was successively washed with water and saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The inorganic salt was filtered off and the solvent was distilled off from the filtrate. The obtained residue was purified over a silicagel column (benzene -→ benzene:ethyl acetate=8:2) to give phenacyl 3-hydroxy-2-n-tetradecyl-11-icosenoate (IV)(998.6 mg, yield 22.1%) in the form of white viscous solid. IR(νmaxKBr, cm-1); 3340, 2900, 2850, 1740, 1705

Workup

  1. customto react for 13.5 hours
  2. filtrationThe insoluble matter in the reaction mixture was filtered off with suction
  3. distillationthe solvent was distilled off from the filtrate
  4. dissolutionThe residue was dissolved in methylene chloride
  5. washthe obtained solution was successively washed with water and saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe inorganic salt was filtered off
  8. distillationthe solvent was distilled off from the filtrate
  9. customThe obtained residue was purified over a silicagel column (benzene -→ benzene:ethyl acetate=8:2)

Sources & evidence

ORD record
ord-2df9f322f0c24fca9dd6ee783b2e70b2
Source dataset
uspto-grants-1991_09
Patent number
US05049664

Reaction notes

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