Thionyl Chloride → HCID 19907981, compound

HRID 1534771Notes

Reaction equation

HRID 1534771 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]O)=[CH:13][CH:12]=1)[CH:2]=[CH2:3].O=S(Cl)[Cl:21]>C(Cl)Cl>[CH2:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][Cl:21])=[CH:13][CH:12]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 54032604HCID 54032604, compound

Product 1

HCID 19907981HCID 19907981, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

All four compounds were prepared by the same method. An example is presented below. 4-[2-(2-Allyloxyethoxy)ethoxy]benzyl alcohol (7.57 g, 0.03 mol) was dissolved in methylene chloride (100 mL), and SOCl2 (4.28 g, 0.036 mol) was added dropwise. After the addition was completed the reaction mixture was stirred at 40° C. for 1 hr. washed with water, 2% NaHCO3 aqueous solution, and water and dried over anhydrous MgSO4. The solvent was evaporated and the residual oil was purified by column chromatography (silica gel, a mixture of 1:3 ethyl acetate to n-hexane as eluent) to yield 6.52 g (80%) of a colorless oily product 14. 1H-NMR (CDCl3, TMS, δ in ppm): 3.55-4.19 (m, 10H, --CH2 --(O--CH2 --CH2)2), 4.55 (s, 2H, Ph--CH2 --), 5.23 and 5.78 (m, 3H, CH2 =CH--), 5.92 and 7.25 (2d, 4 aromatic protons).

Workup

  1. customAll four compounds were prepared by the same method
  2. additionAfter the addition
  3. washwashed with water, 2% NaHCO3 aqueous solution, and water
  4. dry with materialdried over anhydrous MgSO4
  5. customThe solvent was evaporated
  6. customthe residual oil was purified by column chromatography (silica gel
  7. additiona mixture of 1:3 ethyl acetate to n-hexane as eluent)

Sources & evidence

ORD record
ord-7e8da5f55cdf4243b47816a2ab1717b3
Source dataset
uspto-grants-1992_02
Patent number
US05091274

Reaction notes

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