Water → 4-Acetoxy-3,5-di-tert-butylanisole

HRID 23807Notes

Reaction equation

HRID 23807 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:6]=1[OH:17])([CH3:4])([CH3:3])[CH3:2].[C:18](OC(=O)C)(=[O:20])[CH3:19].S(=O)(=O)(O)O.O>C(#N)C>[C:18]([O:17][C:6]1[C:7]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:5]=1[C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 102692,6-Di-tert-butyl-4-methoxyphenol

Product 1

HCID 118219544-Acetoxy-3,5-di-tert-butylanisole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1.50 kg (6.35 mol) of 2,6-di-tert-butyl-4-methoxyphenol and 658 mL (6.98 mol) of acetic anhydride dissolved in 1.2 L of acetonitrile, 3 mL of conc. sulfuric acid was added and the mixture was stirred overnight at room temperature. To the mixture, a great excess of water was added and the resulting solids were filtered and dried. The obtained 4-acetoxy-3,5-di-tert-butylanisole was used in the next reaction without further purification.

Workup

  1. filtrationthe resulting solids were filtered
  2. customdried
  3. customThe obtained 4-acetoxy-3,5-di-tert-butylanisole was used in the next reaction without further purification

Sources & evidence

ORD record
ord-b948cde1a2af422b9f986ffccfac0cfd
Source dataset
uspto-grants-2005_02
Patent number
US06852867B2

Reaction notes

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