Hydrochloric Acid → 1-Bromo-3-(diethoxymethyl)benzene

HRID 1975749Notes

Reaction equation

HRID 1975749 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)C=O.C(O[CH:13]([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])C.Cl>C(O)C>[CH2:18]([O:17][CH:13]([O:14][CH2:15][CH3:16])[C:8]1[CH:7]=[CH:4][CH:3]=[C:2]([Br:1])[CH:9]=1)[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31214Ethyl orthoformateHCID 765833-Bromobenzaldehyde

Product 1

HCID 27335431-Bromo-3-(diethoxymethyl)benzeneYield 108.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 3-bromobenzaldehyde (22.38 g, 121 mmol) in ethanol (150 mL) was added triethylorthoformate (27 g, 181 mmol) and concentrated HCl (0.5 mL). The mixture was heated to reflux for 3 hours and allowed to cool to ambient temperature. The reaction mixture was poured into ice/H2O and extracted thoroughly with hexanes. The combined organic extracts were washed with water and brine, dried (MgSO4) and concentrated in vacuo to give 34 g of 3-bromobenzaldehyde diethyl acetal as a colorless liquid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. extractionextracted thoroughly with hexanes
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0aeb0eb01f4d4f9cb29072ac1d3b9532
Source dataset
uspto-grants-1994_02
Patent number
US05288751

Reaction notes

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