Hydrochloric Acid → 3,5-Di-tert-butyl-2-(methoxymethoxy)benzaldehyde

HRID 22997Notes

Reaction equation

HRID 22997 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:3]=1[O:16][CH2:17][O:18][CH3:19].C([Li])CCC.CN([CH:28]=[O:29])C.Cl>C1COCC1>[C:12]([C:4]1[C:3]([O:16][CH2:17][O:18][CH3:19])=[C:2]([CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=1)[CH:28]=[O:29])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 225926381-Bromo-3,5-bis(1,1-dimethylethyl)-2-(methoxymethoxy)benzeneHCID 178418339Butyllithium

Product 1

HCID 225926103,5-Di-tert-butyl-2-(methoxymethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

46.00 g (140.0 mmol) of the compound obtained in Example 13 (a) and 500 ml of THF are introduced into a three-necked flask under a stream of nitrogen. 61.5 ml (154.00 mmol) of an n-butyllithium solution (2.5M in hexane) are added dropwise at −78° C. and the mixture is stirred for 30 minutes at this same temperature. 13.0 ml (168.0 mmol) of DMF are then added dropwise and the mixture is allowed to return to room temperature. The reaction mixture is acidified with hydrochloric acid (1N) and extracted with ethyl ether and the organic phase is separated by settling, dried over magnesium sulphate and evaporated. 46.00 g (100%) of the expected compound are collected in the form of an orange oil.

Workup

  1. customto return to room temperature
  2. extractionextracted with ethyl ether
  3. customthe organic phase is separated
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. custom46.00 g (100%) of the expected compound are collected in the form of an orange oil

Sources & evidence

ORD record
ord-00f6e9e9be0f4aed8095aeeb6fc4df28
Source dataset
uspto-grants-2005_02
Patent number
US06849658B2

Reaction notes

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