Ethanol → HCID 86669338, compound

HRID 1844532Notes

Reaction equation

HRID 1844532 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH2:11][CH2:12][OH:13].[N+:14]([O-])([OH:16])=[O:15].CCO>C(O)(=O)C>[OH:1][C:2]1[C:9]([N+:14]([O-:16])=[O:15])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH2:11][CH2:12][OH:13]

Participants

5

Reactant 3

HCID 702EthanolHCID 944Nitric AcidHCID 86669353HCID 86669353, compound

Product 1

HCID 86669338HCID 86669338, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of 4-hydroxy-3-(2-hydroxyethoxy)benzaldehyde in acetic acid (5 mL) was added 65% nitric acid (34.6 mg, 0.55 mmol) at 0° C., and the mixture was stirred at 0° C. 4 hours. The reaction mixture was poured into ice water followed by a standard aqueous/EtOH workup. Isolated 110 mg, yield 88.7% of Intermediate 10.

Workup

  1. custom4 hours

Sources & evidence

ORD record
ord-fd8f33e7089b489d80f3a32f5fe96361
Source dataset
uspto-grants-2015_02
Patent number
US08946434B2

Reaction notes

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