Acetyl chloride → HCID 22918665, compound

HRID 1452365Notes

Reaction equation

HRID 1452365 reaction equation
[C:1]([C:5]1[C:10]([CH3:11])=[C:9]([O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[CH:8]=[C:7]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:6]=1[OH:23])([CH3:4])([CH3:3])[CH3:2].CCCCCC.C([Li])CCC.[C:35](Cl)(=[O:37])[CH3:36].[Cl-].[NH4+]>O1CCCC1>[C:35]([O:23][C:6]1[C:7]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:8][C:9]([O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)=[C:10]([CH3:11])[C:5]=1[C:1]([CH3:3])([CH3:4])[CH3:2])(=[O:37])[CH3:36]

Participants

7

Reactant 5

HCID 6367Acetyl chlorideHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 22918662HCID 22918662, compoundHCID 178418339Butyllithium

Product 1

HCID 22918665HCID 22918665, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,6-Di-tert-butyl-3-methyl-4-tetrahydropyranyloxyphenol (4.4 g) was dissolved in anhydrous tetrahydrofuran (50 ml) and a n-hexane solution (1.1 eq.) of n-butyllithium was added dropwise at 0° C. under a nitrogen atmosphere. After stirring the mixture for 30 min, acetyl chloride (1.08 ml, 1.1 eq.) was added and the mixture was allowed to warm to room temperature. After stirring for 3 h, the reaction mixture was poured into a saturated aqueous solution of ammonium chloride and the mixture was subjected to extraction with diethyl ether. The extract was washed with water and saturated brine, then dried over anhydrous sodium sulfate and the solvent was distilled off. The residue was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 1-acetoxy-2,6-di-tert-butyl-3-methyl-4-tetrahydropyranyloxybenzene [4.09 g (yield, 82.2%)] as a colorless crystal.

Workup

  1. stirringAfter stirring for 3 h
  2. extractionthe mixture was subjected to extraction with diethyl ether
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by silica gel chromatography (10% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-9a3b51a6598943eeb04b5fa3036f1fdc
Source dataset
uspto-grants-1997_02
Patent number
US05606089

Reaction notes

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