Methanol → 1-[1,1-Bis(methyloxy)ethyl]-4-tert-butylbenzene

HRID 607527Notes

Reaction equation

HRID 607527 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:13])[CH3:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH:14](OC)(OC)[O:15]C.[CH3:21]O>[Br-].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:21][O:13][C:11]([C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=1)([O:15][CH3:14])[CH3:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 9005Trimethyl orthoformateHCID 13669p-tert-Butylacetophenone

Product 1

HCID 687141071-[1,1-Bis(methyloxy)ethyl]-4-tert-butylbenzene

Reagents, catalysts & solvents 1

HCID 23500184Tetra-n-butylammonium tribromideCatalyst

Procedure

To a stirred solution of 4′-tert-butylacetophenone (purchased from Aldrich, 1.76 g, 10 mmol) in MeOH (1 mL) was added trimethyl orthoformate (1.97 g, 11 mmol) and tetrabutylammonium tribromide (48.2 mg, 0.1 mmol) successively. The same reaction procedure as described in Example 63A was performed to give the title compound (2.33 g) as a yellow oil.

Workup

  1. customThe same reaction procedure

Sources & evidence

ORD record
ord-3906cc8263614b3389b5d48feee77f4a
Source dataset
uspto-grants-2011_03
Patent number
US07915448B2

Reaction notes

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