Iodine → HCID 21526363, compound

HRID 1659071Notes

Reaction equation

HRID 1659071 reaction equation
[OH:1][CH:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].II.[Cl:24]Cl>C(Cl)(Cl)(Cl)Cl>[OH:1][CH:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:12]([Cl:24])[CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 807IodineHCID 24526ChlorineHCID 21526310HCID 21526310, compound

Product 1

HCID 21526363HCID 21526363, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
0 °C

Procedure

Ethyl α-hydroxy-γ-(4-cyclohexylphenyl)butyrate 0.38 mole and 6.1 g. of iodine (0.048 mole) and dissolved in 100 ml. of carbon tetrachloride. To this solution is added a solution of 40.4 g. (0.57 mole) of chlorine dissolved in 365 ml. of carbon tetrachloride over a period of 2 hours. During the addition, the temperature of the reaction mixture is maintained at 0°C. The mixture is stirred for 3 hours and allowed to stand with gradual warming to room temperature over 15 hours. The solvent is removed by distillation under reduced pressure. The residue is fractionally distilled to obtain ethyl α-hydroxy-γ-(3-chloro-4-cyclohexylphenyl)butyrate.

Workup

  1. additionTo this solution is added a solution of 40.4 g
  2. additionDuring the addition
  3. temperaturewith gradual warming to room temperature over 15 hours
  4. customThe solvent is removed by distillation under reduced pressure
  5. distillationThe residue is fractionally distilled

Sources & evidence

ORD record
ord-f17aae2d719641d6bd97d0ffdfb0ec0a
Source dataset
uspto-grants-1976_06
Patent number
US03966801

Reaction notes

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