Thionyl Chloride → 4-Benzyloxy-3-nitrobenzyl chloride

HRID 1032513

Reaction equation

[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]O)=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:22])=O>>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][Cl:22])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 13629301(4-(Benzyloxy)-3-nitrophenyl)methanol

Product 1

HCID 136293024-Benzyloxy-3-nitrobenzyl chloride

Procedure

Under agitation, 58.3 g of 4-benzyloxy-3-nitrobenzyl alcohol is introduced in incremental portions into 250 ml of thionyl chloride, stirred for 30 minutes at room temperature, and concentrated under vacuum. The residue is recrystallized from diisopropyl ether while decolorizing with active carbon, thus producing 50.9 g of 4-benzyloxy-3-nitrobenzyl chloride, mp 60°-61° C.

Workup

concentrationconcentrated under vacuum
customThe residue is recrystallized from diisopropyl ether

Sources & evidence

ORD record: ord-f154fe0b6dc34555ac16b885a6de168a
Source dataset: uspto-grants-1990_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04958026

Linked notes

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