Carbon Tetrachloride → HCID 18761413, compound

HRID 431714Notes

Reaction equation

HRID 431714 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Cl:24])(Cl)(Cl)Cl.[CH2:25]([O:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39]CO)=[C:35]([N+:42]([O-:44])=[O:43])[CH:34]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)Cl>[CH2:25]([O:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:20][Cl:24])=[C:35]([N+:42]([O-:44])=[O:43])[CH:34]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 18761444HCID 18761444, compound

Product 1

HCID 18761413HCID 18761413, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (1.98 g, 7.55 mmol), CCl4 (2.18 mL, 22.62 mmol), and dry CH2Cl2 (13.7 mL) were added to 2-(4-benzyloxy-2-nitrophenyl)ethanol (1.03 g, 3.77 mmol) in a round bottom flask. A red solution with pink precipitate formed, but dissolved after 30 min. The solution was allowed to stir overnight under positive pressure of nitrogen. The solution was checked by TLC (20% ethyl acetate/petroleum ether) and then concentrated using a rotoevaporator. The brown oily residue was purified using silica gel column chromatography and a 10% ethyl acetate, 5% CHCl3, and 85% petroleum ether solvent system. 2-(4-Benzyloxy-2-nitrophenyl)ethyl chloride was isolated as a thick yellowish oil which solidified upon standing in the refrigerator (1.06 g, 3.64 mmol, 97% yield). Mp 38-40° C.; TLC (20% ethyl acetate/hexane) Rf=0.53; 1H-NMR (500 MHz, CDCl3) 7.51 (d, 2.5, 1H), 7.33 (m, 5H), 7.23 (d, 8.5, 1H), 7.10 (dd, 2.5, 8.5, 1H), 5.02 (s, 2H), 3.70 (t, 7.0, 2H), 3.20 (t, 7.0, 2H); 13C-NMR (125 MHz, CDCl3) 158.1, 149.5, 135.7, 143.0, 128.7, 128.4, 127.5, 125.1, 120.4, 110.7, 70.6, 44.0, 35.8; IR (neat) 3092, 3038, 2962, 2919, 2865, 1618, 1570, 1532, 1499, 1451, 1343, 1294, 1197, 1160, 1062, 1019, 906, 847, 809, 739, 696, 652; EI-MS m/z (relative intensity) 291 (M+, 10); isotope pattern of M+ and M++2 agrees with the presence of one chlorine atom. Accurate mass (EI-MS) for C15H1435ClNO3: calcd. 291.0662, obsd. 291.0667.

Workup

  1. customA red solution with pink precipitate formed
  2. dissolutiondissolved after 30 min
  3. concentrationconcentrated
  4. customThe brown oily residue was purified

Sources & evidence

ORD record
ord-a446ef754b8944198ed821104ec640af
Source dataset
uspto-grants-2003_12
Patent number
US06660742B2

Reaction notes

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