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

HRID 1438405Notes

Reaction equation

HRID 1438405 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 (purcashed 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-3c9f96d7886b4a3a99220f540f97a79b
Source dataset
uspto-grants-2009_11
Patent number
US07622589B2

Reaction notes

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