Ethylene Glycol → HCID 53782660, compound

HRID 365645Notes

Reaction equation

HRID 365645 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:13](O)[CH2:14][OH:15].B(F)(F)F.CCOCC>C(O)(=O)C>[CH2:14]1[O:15][CH:4]([C:3]2[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:2]=2[F:1])[O:5][CH2:13]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 3283Diethyl EtherHCID 6356Boron trifluorideHCID 27347702-Fluoro-5-nitrobenzaldehyde

Product 1

HCID 53782660HCID 53782660, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 2-fluoro-5-nitro-benzaldehyde (25.0 g, 148 mmol), ethylene glycol (160 mL, 2.87 mol) in acetic acid (625 mL) was heated to 55° C. for 15 min. The temperature was then adjusted to 45° C., at which time BF3 --Et2O (20 mL, 20 mmol) was added dropwise (30 min). After an additionl 60 min at 45° C. the solution was cooled to room temperature, and poured onto ice (1 L). The resulting solid was filtered, pressed dry, and dried in vacuo to afford the title compound as white flakes (18.81 g, 60%). MS(ES) m/e 213 [M+H]+.

Workup

  1. additionpoured onto ice (1 L)
  2. filtrationThe resulting solid was filtered
  3. custompressed dry
  4. customdried in vacuo

Sources & evidence

ORD record
ord-27221d6c075e4787bddfdfd8c4adcd8d
Source dataset
uspto-grants-2000_10
Patent number
US06127359

Reaction notes

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