4-Nitrobenzaldehyde → 5-(4-Nitrophenyl)-1,3-dioxolo[4,5-g]-isochroman

HRID 430653Notes

Reaction equation

HRID 430653 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][OH:12])=[CH:9][C:4]=2[O:3][CH2:2]1.[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1)([O-:15])=[O:14]>C(O)C>[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH:20]2[C:7]3[CH:6]=[C:5]4[O:1][CH2:2][O:3][C:4]4=[CH:9][C:8]=3[CH2:10][CH2:11][O:12]2)=[CH:18][CH:17]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 5414-NitrobenzaldehydeHCID 27598462-(1,3-Dioxaindan-5-yl)ethan-1-ol

Product 1

HCID 4042105-(4-Nitrophenyl)-1,3-dioxolo[4,5-g]-isochromanYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

36.0 g (0.21 mol) of 2-(1,3-benzodioxol-5-yl)-ethanol is reacted with an equivalent amount of 4-nitrobenzaldehyde analogously to C.A. 105, 1986, 226357, and 50.7 g (81%) of the title compound, melting point 149-150° C. (ethanol), is obtained.

Sources & evidence

ORD record
ord-4240d1d38a9f4944846de6d24e713ac3
Source dataset
uspto-grants-2001_11
Patent number
US06323197B1

Reaction notes

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