3-Chloro-2-methyl-1-propene → HCID 11726907, compound

HRID 1376972Notes

Reaction equation

HRID 1376972 reaction equation
[H-].[Na+].[C:3]([O:6][C:7]1[C:12]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:11][C:10]([OH:17])=[CH:9][C:8]=1[C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:5])[CH3:4].Cl[CH2:23][C:24]([CH3:26])=[CH2:25].[Cl-].[NH4+]>CN(C)C=O>[C:3]([O:6][C:7]1[C:12]([C:13]([CH3:14])([CH3:16])[CH3:15])=[CH:11][C:10]([O:17][CH2:25][C:24]([CH3:26])=[CH2:23])=[CH:9][C:8]=1[C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:5])[CH3:4]

Participants

6

Reactant 4

HCID 112413-Chloro-2-methyl-1-propeneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 111399982,6-DI-Tert-butyl-4-hydroxyphenyl acetate

Product 1

HCID 11726907HCID 11726907, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

60% Oily sodium hydride (0.18 g) was suspended in N,N-dimethylformamide (16 ml). A solution of 4-acetoxy-3,5-di-tert-butylphenol (1 g) in N,N-dimethylformamide (5 ml) was added dropwise to the suspension under ice cooling and the mixture was stirred for 30 min. Subsequently, the reaction mixture was allowed to warm to room temperature and 3-chloro-2-methyl-1-propene (0.45 ml) was added dropwise. After stirring at room temperature for 2 h, a saturated aqueous solution of ammonium chloride (15 ml) was added to the reaction mixture. The mixture was subjected to extraction with diethyl ether and the organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 4-acetoxy-3,5-di-tert-butyl-1-(2-methyl-2-propenyloxy)benzene [1.08 g (yield, 90%)] as a colorless liquid.

Workup

  1. stirringAfter stirring at room temperature for 2 h
  2. extractionThe mixture was subjected to extraction with diethyl ether
  3. washthe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-0a4f223d74a44214baf3ca06a2c6caab
Source dataset
uspto-grants-1997_09
Patent number
US05663373

Reaction notes

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