Bicarbonate Ion → 1-Bromo-4-(dimethoxymethyl)benzene

HRID 1938147Notes

Reaction equation

HRID 1938147 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10](=[O:13])(O)[O-].[CH3:14]O>S(Cl)(Cl)=O>[CH3:14][O:7][CH:6]([O:13][CH3:10])[C:5]1[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 769Bicarbonate IonHCID 887MethanolHCID 707414-Bromobenzaldehyde

Product 1

HCID 6883421-Bromo-4-(dimethoxymethyl)benzene

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent2×

Procedure

50 g of 4-bromobenzaldehyde and 30 ml of o-triethyl formate are agitated for 5 hours at room temperature in 60 ml of methanol and 0.8 ml of thionyl chloride. After that, another 0.2 ml of thionyl chloride are added. The batch is poured into aqueous bicarbonate solution after 30 minutes and extracted with chloroform, washed with aqueous bicarbonate solution and water, dried above sodium sulfate, and concentrated by evaporation under reduced pressure. 68 g of 4-bromobenzaldehyde dimethyl ketal are obtained in the form of colourless oil.

Workup

  1. extractionextracted with chloroform
  2. washwashed with aqueous bicarbonate solution and water
  3. dry with materialdried above sodium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-57cd6d343b11454cb3a908a663b7c964
Source dataset
uspto-grants-1997_12
Patent number
US05693628

Reaction notes

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