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Sodium hydride → 4-Acetoxy-3,5-di-tert-butyl-2-(1-hydroxy-2-pentylheptyl)phenol

HRID 23802
Notes
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Reaction equation

HRID 23802 reaction equation
[H-].[Na+].[C:3]([O:6][C:7]1[C:8]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:9][C:10]([OH:19])=[C:11]([C:14]=1[C:15]([CH3:18])([CH3:17])[CH3:16])[CH:12]=[O:13])(=[O:5])[CH3:4].[CH3:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]([Mg]Cl)[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].[Cl-].[NH4+]>O1CCCC1>[C:3]([O:6][C:7]1[C:8]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:9][C:10]([OH:19])=[C:11]([CH:12]([OH:13])[CH:29]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:28][CH2:27][CH2:26][CH2:25][CH3:24])[C:14]=1[C:15]([CH3:16])([CH3:18])[CH3:17])(=[O:5])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 110445455-Acetoxy-4,6-di-tert-butyl-2-hydroxybenzaldehydeHCID 178444616HCID 178444616, compound

Product 1

HCID 110808364-Acetoxy-3,5-di-tert-butyl-2-(1-hydroxy-2-pentylheptyl)phenol

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

In a nitrogen atmosphere, 270 mL of tetrahydrofuran was added to 13.0 g (0.33 mol) of 60% sodium hydride under cooling with ice; to the mixture, 94.5 g (0.32 mol) of 5-acetoxy-4,6-di-tert-butyl-2-hydroxybenzaldehyde in 200 mL of tetrahydrofuran was added dropwise and the mixture was stirred for 1 hour at room temperature. Thereafter, the Grignard reagent prepared in Example 6 was added dropwise to the mixture, which was subjected to reaction for 1 hour at room temperature. Under cooling with ice, 1000 mL of a saturated aqueous solution of ammonium chloride was added and the mixture was extracted twice with 1000 mL of ethyl acetate. The organic layer was washed with 1000 mL of a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After filtering off the magnesium sulfate, the filtrate was concentrated and the concentrate was dissolved in 1000 mL of hexane under heating. Thereafter, the solution was slowly cooled down to 0° C. for crystallization and the crystal was separated and dried to give 85.6 g of 4-acetoxy-3,5-di-tert-butyl-2-(1-hydroxy-2-pentylheptyl)phenol.

Workup

  1. temperatureunder cooling with ice
  2. customwas subjected to reaction for 1 hour at room temperature
  3. additionwas added
  4. extractionthe mixture was extracted twice with 1000 mL of ethyl acetate
  5. washThe organic layer was washed with 1000 mL of a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtering off the magnesium sulfate
  8. concentrationthe filtrate was concentrated
  9. dissolutionthe concentrate was dissolved in 1000 mL of hexane
  10. temperatureunder heating
  11. temperatureThereafter, the solution was slowly cooled down to 0° C. for crystallization
  12. customthe crystal was separated
  13. customdried

Sources & evidence

ORD record
ord-01fc00bd8602418ca85792d26eabc102
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06852867B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes