Dichloromethane → 11-Chloro-1-undecene

HRID 231350

Reaction equation

HRID 231350 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].O=S(Cl)[Cl:15].C(Cl)Cl>N1C=CC=CC=1.O>[CH2:1]([Cl:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 818510-Undecen-1-olHCID 24386Thionyl Chloride

Product 1

HCID 54380511-Chloro-1-undeceneYield 84.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 100 g (0.588 mole) of 10-undecenyl alcohol and 2 g of pyridine was added 75 g (0.63 mole) of SOCl2 dropwise over a period of 45 minutes at 25° C. The solution was heated at 65° C. for 5 hours. CH2Cl2 (100 mL) was added and the solution was water washed twice, dried with MgSO4, filtered, and the CH2Cl2 evaporated. The residue (103 g) by GC analysis showed a purity of 99.3% VIII with 0.7% alcohol; IR showed no OH band and absorbence at 1641-1. Distillation (15.24 centimeter jacketed Vigreaux column) gave 94 g VIII (bp 104°-105° C. at 6 mm) (GC showed no alcohol; 100% VIII).

Workup

  1. washwashed twice
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customthe CH2Cl2 evaporated
  5. distillationDistillation (15.24 centimeter jacketed Vigreaux column)

Sources & evidence

ORD record
ord-5d598318549b483b9d8cee0ddc53e0bd
Source dataset
uspto-grants-1989_07
Patent number
US04845271

Linked notes

Loading…