Acetic Anhydride → 3-chloro-5-(3-iodopropyl)-5H-dibenzo[a,d]cycloheptene

HRID 1576610Notes

Reaction equation

HRID 1576610 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]=[CH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH:7]([CH2:16][CH2:17][CH2:18]OCC)[C:6]=2[CH:22]=1.C(OC(=O)C)(=O)C.[IH:30]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:11]=[CH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH:7]([CH2:16][CH2:17][CH2:18][I:30])[C:6]=2[CH:22]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 24841Hydrogen iodideHCID 214120893-chloro-5-(3-ethoxypropyl)-5H-dibenzo[a,d]cycloheptene

Product 1

HCID 214121133-chloro-5-(3-iodopropyl)-5H-dibenzo[a,d]cycloheptene

Conditions

Temperature
65 °C

Procedure

3-Chloro-5-(3-ethoxypropyl)-5H-dibenzo[a,d]cycloheptene (0.03 mole) is dissolved in 45 ml. of acetic anhydride. The solution is heated to 65°C. and nitrogen is passed through while 30 ml. of hydriodic acid (sp. gr., 1.5) is added gradually, keeping the temperature below 90°C. The solution is heated to approximately 80°C. for 30 minutes, then cooled and poured into ice-water. The product is extracted into ether, the extract washed with dilute sodium thiosulfate solution, followed by dilute sodium bicarbonate solution and finally with water. The product is isolated by evaporation of the ether.

Workup

  1. customthe temperature below 90°C
  2. temperatureThe solution is heated to approximately 80°C. for 30 minutes
  3. temperaturecooled
  4. extractionThe product is extracted into ether
  5. washthe extract washed with dilute sodium thiosulfate solution
  6. customThe product is isolated by evaporation of the ether

Sources & evidence

ORD record
ord-c463ee3110f841c49b1e8922f2a8d9e0
Source dataset
uspto-grants-1976_09
Patent number
US03981917

Reaction notes

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