Iodine → HCID 66615148, compound

HRID 2046135Notes

Reaction equation

HRID 2046135 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[I:16]I>C(Cl)Cl>[I:16][C:13]1[CH:14]=[C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH:10]=[CH:11][C:12]=1[OH:15]

Participants

4

Reactant 2

HCID 807IodineHCID 157304-Octylphenol

Product 1

HCID 66615148HCID 66615148, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-octyl phenol (0.15 g, 0.73 mmol), CF3CO2Ag (0.25 g, 1 mmol) and I2 (0.185 g, 0.73 mmol) in CH2Cl2 (10 ml) was stirred for 0.5 h at 0° C., then for 0.5 h at room temperature. The solution was filtered through Celite bead and washed with CH2Cl2 (30 ml). The filtrates were evaporated to dryness to give the title compound (0.21 g, 87%) as fawn oil. 1H NMR (CDCl3) 7.32 (d, 1H, J=8.34 Hz); 7.28 (d, 1H, J=1.26 Hz); 6.98 (dd, 1H, 8.37, 1.71 Hz); 6.62 (s, 1H); 4.69 (t, 2H, J=5.88 Hz); 3.62-3.38 (m, 4H); 2.59 (t, 2H, J=7.29 Hz); 1.56-1.51 (m, 2H); 1.34-1.2 (m, 10H); 0.81 (t, 3H, J=6.48 Hz).

Workup

  1. waitfor 0.5 h at room temperature
  2. filtrationThe solution was filtered through Celite bead
  3. washwashed with CH2Cl2 (30 ml)
  4. customThe filtrates were evaporated to dryness

Sources & evidence

ORD record
ord-c7f9f88fb4264c25a2666d1eb7f7f88d
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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