Phenacyl bromide → HCID 54398312, compound

HRID 728745Notes

Reaction equation

HRID 728745 reaction equation
[CH2:1]([CH:15]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]CCCC)[C:16]([OH:18])=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH2:39](Br)[C:40]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:41].C(N(CC)CC)C.[O:56]1CCCC1>>[OH:56][CH:19]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:15]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:16]([O:18][CH2:39][C:40]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:41])=[O:17]

Participants

5

Reactant 4

HCID 6259Phenacyl bromideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 21275969HCID 21275969, compound

Product 1

HCID 54398312HCID 54398312, compoundYield 33%

Procedure

3-Hydroxy-2-n-tetradecyl-octadecanoic acid (II) prepared as described [Bulletin de la Societe chimique de France 504-510 (1954)] was dissolved in dry tetrahydrofuran (45 ml), and then phenacyl bromide (2.70 g, 13.59 millimole) and triethyl amine (1.89 ml, 13.59 millimole) were successively added thereto with ice cooling. The mixture was allowed to warm to the room temperature, and reacted for 23 hours. The insoluble mass in the reaction mixture was filtered off with suction and the solvent was distilled from the filtrate. The residue was dissolved in benzene and the obtained solution was fractionated through silicagel column chromatography (benzene). After the fractions comprising impurities were discarded, the later colorless fractions were pooled, and the solvent was distilled off from the fraction to, give white crystals of phenacyl 3-hydroxy-2-n-tetradecyl-octadecanoate (IV) (1.81 g, yield 33%).

Workup

  1. customreacted for 23 hours
  2. filtrationThe insoluble mass in the reaction mixture was filtered off with suction
  3. distillationthe solvent was distilled from the filtrate
  4. dissolutionThe residue was dissolved in benzene
  5. distillationthe solvent was distilled off from the fraction to,

Sources & evidence

ORD record
ord-454e7029a4b6401f8956e1f4d5ed1225
Source dataset
uspto-grants-1991_09
Patent number
US05049664

Reaction notes

Loading…