Acetyl chloride → HCID 22918665, compound

HRID 1376981Notes

Reaction equation

HRID 1376981 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-d947c78d730c4a64a2122b9597c89aab
Source dataset
uspto-grants-1997_09
Patent number
US05663373

Reaction notes

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