1-Iodopropane → HCID 15027158, compound

HRID 274172Notes

Reaction equation

HRID 274172 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH:17]([OH:19])[CH3:18])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH2:20](I)[CH2:21][CH3:22]>C(Cl)(Cl)Cl.[Ag].[Ag]=O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH:17]([O:19][CH2:20][CH2:21][CH3:22])[CH3:18])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 336431-IodopropaneHCID 15027157HCID 15027157, compound

Product 1

HCID 15027158HCID 15027158, compoundYield 30.5%

Reagents, catalysts & solvents 3

HCID 92152Silver(II) oxideCatalystHCID 6212ChloroformSolvent2×HCID 23954SilverSolvent

Procedure

Into a four-necked flask provided with a stirrer and a thermometer, 25.4 g of (-)-4-acetyl-4'-(2-hydroxypropyl)biphenyl (XXIII-43) [0.1 mol, [α]D20 =-11.2° (C=1, CHCl3)], 69.5 g (0.3 mol) of silver oxide and 255 g (1.5 mol) of propyl iodide were charged, and then stirred at room temperature for 15 days. Thereafter, the reaction mixture was diluted with 300 ml of chloroform, and silver salt was filtered off, and thereafter, the filtrate was concentrated under a reduced pressure. The resulting residue was subjected to a silica gel column chromatography (elution medium: toluene/ethyl acetate=10/1) to obtain 9.0 g of (-)-4-acetyl-4'-(2-propoxypropyl) biphenyl (XXII-43) [yield=30.5%, [α]D20 =-10.2° (C=1, CHCl3), m.p.=5320 -55° C.] and 17.4 g of the starting material (XXIII-43) with recovery of 68.5%.

Workup

  1. customInto a four-necked flask provided with a stirrer
  2. filtrationwas filtered off
  3. concentrationthe filtrate was concentrated under a reduced pressure
  4. washThe resulting residue was subjected to a silica gel column chromatography (elution medium: toluene/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-9bfe5261cee0435595e0389ee68d9db6
Source dataset
uspto-grants-1995_02
Patent number
US05389293

Reaction notes

Loading…