Neopentyl alcohol → HCID 22118163, compound

HRID 355303Notes

Reaction equation

HRID 355303 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:5]=1[CH:6]([OH:10])[C:7]([OH:9])=[O:8])([O-:3])=[O:2].[CH2:18](O)[C:19]([CH3:22])([CH3:21])[CH3:20]>OS(O)(=O)=O>[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:5]=1[CH:6]([OH:10])[C:7]([O:9][CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:8])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6404Neopentyl alcoholHCID 22118165HCID 22118165, compound

Product 1

HCID 22118163HCID 22118163, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

2,6-dinitromandelic acid (4.00 g, 16.5 mmol) was added to an excess of neopentyl alcohol (20.0 g, 227 mmol) melted in a round bottom flask. To this solution was added 5 drops of H2SO4 and it was heated to reflux for 3 hours. The excess neopentyl alcohol was removed under reduced pressure, and the residue was purified by column chromatography over silica gel (60-200 mesh) using methylene chloride/hexane (1:1) as the eluant. The yield after two recrystallizations from CHCl3 /petroleum ether was 3.8 g (74%).

Workup

  1. custommelted in a round bottom flask
  2. temperaturewas heated
  3. temperatureto reflux for 3 hours
  4. customThe excess neopentyl alcohol was removed under reduced pressure
  5. customthe residue was purified by column chromatography over silica gel (60-200 mesh)
  6. customThe yield
  7. customafter two recrystallizations from CHCl3 /petroleum ether

Sources & evidence

ORD record
ord-f63ac26ce7bd4160ba67c48c8459c151
Source dataset
uspto-grants-1998_11
Patent number
US05830619

Reaction notes

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