Thionyl Chloride → HCID 20432997, compound

HRID 371791Notes

Reaction equation

HRID 371791 reaction equation
[CH2:1]([O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:11]O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].S(Cl)([Cl:25])=O>>[CH2:1]([O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:11][Cl:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 54068979HCID 54068979, compound

Product 1

HCID 20432997HCID 20432997, compound

Procedure

Thionyl chloride (140 ml.) and 3,4-dihexoxybenzyl alcohol (14.0 g.) are combined and stirred at room temperature for 1/2 hour, at which time gas evolution ceases. The mixture is refluxed for one-half hour and then distilled to remove thionyl chloride (about 100 ml.). The residue is poured into ice-water (250 g. of each) and the aqueous solution extracted with chloroform (3 × 100 ml.). The chloroform extracts are combined, washed successively with saturated sodium bicarbonate solution (2 × 100 ml.) and water (3 × 100 ml.). It is then dried (Na2SO4) and concentrated to give 3,4-dihexoxybenzyl chloride as a brown oil (11.7 g.).

Workup

  1. temperatureThe mixture is refluxed for one-half hour
  2. distillationdistilled
  3. customto remove thionyl chloride (about 100 ml.)
  4. additionThe residue is poured into ice-water (250 g
  5. extractionof each) and the aqueous solution extracted with chloroform (3 × 100 ml.)
  6. washwashed successively with saturated sodium bicarbonate solution (2 × 100 ml.) and water (3 × 100 ml.)
  7. dry with materialIt is then dried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0ad7297bfd5a46fbacd6c75afcc351c9
Source dataset
uspto-grants-1978_05
Patent number
US04087552

Reaction notes

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