Ethylene Glycol → HCID 53782660, compound

HRID 1938770Notes

Reaction equation

HRID 1938770 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

5

Reactant 3

HCID 174Ethylene GlycolHCID 8000Boron trifluoride etherateHCID 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 additional 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. additionwas added dropwise (30 min)
  2. additionpoured onto ice (1 L)
  3. filtrationThe resulting solid was filtered
  4. custompressed dry
  5. customdried in vacuo

Sources & evidence

ORD record
ord-a482d8c99b464373817963ddbb9044a5
Source dataset
uspto-grants-1997_12
Patent number
US05693636

Reaction notes

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