1,3-Propanediol → 2-(3-Hydroxy-4-nitro-phenyl)-1,3-dioxane

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH:5]=[O:6].[CH2:13](O)[CH2:14][CH2:15][OH:16]>>[OH:1][C:2]1[CH:3]=[C:4]([CH:5]2[O:16][CH2:15][CH2:14][CH2:13][O:6]2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11]

Participants

Reactant 2

HCID 104421,3-Propanediol

HCID 697123-Hydroxy-4-nitrobenzaldehyde

Product 1

HCID 212639072-(3-Hydroxy-4-nitro-phenyl)-1,3-dioxaneYield 95%

Procedure

3-Hydroxy-4-nitro-benzaldehyde (7.5 g, 44.9 mmol) is treated with 1,3-propanediol (5.1 g, 67.3 mmol) according to the procedure of Example 1 to give 2-(3-hydroxy-4-nitro-phenyl)-1,3-dioxane (9.6 g, 95% yield) oil.

Sources & evidence

ORD record: ord-47fd00c473444ceaa542dbf3e5af84a5
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06177422B1

Reaction notes

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