Thionyl Chloride → HCID 68134844, compound

HRID 268043

Reaction equation

HRID 268043 reaction equation
[CH:1]1[C:6](/[CH:7]=[CH:8]/[C:9]([OH:11])=[O:10])=[CH:5][CH:4]=[C:3]([Cl:12])[CH:2]=1.S(Cl)(Cl)=O.[CH2:17]([N:19]([CH2:26][CH3:27])[CH2:20][C:21]([CH3:25])([CH3:24])[CH2:22]O)[CH3:18]>C1C=CC=CC=1>[ClH:12].[CH2:17]([N:19]([CH2:26][CH3:27])[CH2:20][C:21]([CH3:25])([CH3:24])[CH2:22][C:7]([C:6]1[CH:5]=[CH:4][C:3]([Cl:12])=[CH:2][CH:1]=1)=[C:8]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:9]([OH:11])=[O:10])[CH3:18]

Participants

5

Reactant 3

HCID 24386Thionyl Chloride2×HCID 2959653-(Diethylamino)-2,2-dimethylpropan-1-olHCID 6377974-Chlorocinnamic acid

Product 1

HCID 68134844HCID 68134844, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

P-Chlorocinnamic acid (27.5 g, 0.15 mole) was added with rapid stirring to thionyl chloride (52.5 ml) and refluxed for 31/2 hours. The mixture was stripped of excess thionyl chloride under reduced pressure, benzene (100 ml) was added and the mixture was again stripped of solvent. The residue was treated with a solution of 3-diethylamino-2,2-dimethylpropanol (24.2 g, 0.15 mole) in benzene (500 ml), refluxed for 3 hours, cooled, diluted with petroleum ether (500 ml), and stored overnight at room temperature. The benzene-petroleum ether solution was decanted, the residue dissolved in H2O (700 ml) and the solution adjusted to pH 10 with saturated aqueous K2CO3 (60 ml). The product was extracted from the aqueous phase with benzene (800 ml) in portions and the extract dried overnight over MgSO4 and Darco. The solution was filtered and the filtrate adjusted to pH 2 with a solution of dry HCl in ether (cooled in an ice bath). Petroleum ether (500 ml) was added and the product oiled out of solution. The benzene-petroleum ether solution was decanted and the product was recrystallized from ethyl acetate (600 ml), yield: 33 g (61%). A sample was recrystallized from ethyl acetate, m.p. 132°-134°.

Workup

  1. temperaturerefluxed for 31/2 hours
  2. additionwas added
  3. temperaturerefluxed for 3 hours
  4. temperaturecooled
  5. customThe benzene-petroleum ether solution was decanted
  6. dissolutionthe residue dissolved in H2O (700 ml)
  7. extractionThe product was extracted from the aqueous phase with benzene (800 ml) in portions
  8. dry with materialthe extract dried overnight over MgSO4 and Darco
  9. filtrationThe solution was filtered
  10. additionPetroleum ether (500 ml) was added
  11. customThe benzene-petroleum ether solution was decanted
  12. customthe product was recrystallized from ethyl acetate (600 ml), yield: 33 g (61%)
  13. customA sample was recrystallized from ethyl acetate, m.p. 132°-134°

Sources & evidence

ORD record
ord-c97a9d536b1449da98bcfd645ef1d0af
Source dataset
uspto-grants-1976_03
Patent number
US03946042

Linked notes

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