Thionyl Chloride → HCID 22120979, compound

HRID 1274367Notes

Reaction equation

HRID 1274367 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]([O:13][C:14]2[CH:21]=[CH:20][C:17]([CH2:18]O)=[CH:16][C:15]=2[N+:22]([O-:24])=[O:23])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:29])=O>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]([O:13][C:14]2[CH:21]=[CH:20][C:17]([CH2:18][Cl:29])=[CH:16][C:15]=2[N+:22]([O-:24])=[O:23])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 53849665HCID 53849665, compound

Product 1

HCID 22120979HCID 22120979, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-[4-(benzyloxy)-phenoxy]-3-nitrobenzyl alcohol (9.43 g, 26.9 mmol) in chloroform (60 ml) was added thionyl chloride (2 ml), followed by stirring at room temperature for 6 hours. After allowing to stand overnight, the reaction solution was washed with water and dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography [eluent; hexane - chloroform (1:1)] to give 4-[4-(benzyloxy)-phenoxy]-3-nitrobenzyl chloride (7.63 g).

Workup

  1. waitto stand overnight
  2. washthe reaction solution was washed with water
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography [eluent; hexane - chloroform (1:1)]

Sources & evidence

ORD record
ord-50f9cb3aa50d47e4bb273e8862a2bb9a
Source dataset
uspto-grants-2000_12
Patent number
US06156801

Reaction notes

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