Ethyl orthoformate → 5-Bromo-1-diethoxymethyl-3-isopropyl-2-methoxybenzene

HRID 385039Notes

Reaction equation

HRID 385039 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]([CH3:14])[CH3:13])[C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)C=O.[CH:15]([O:22][CH2:23][CH3:24])([O:19][CH2:20][CH3:21])OCC>CCCCCC>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]([CH3:14])[CH3:13])[C:5]([O:10][CH3:11])=[C:6]([CH:15]([O:19][CH2:20][CH3:21])[O:22][CH2:23][CH3:24])[CH:9]=1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 840479705-Bromo-3-isopropyl-2-methoxybenzaldehyde

Product 1

HCID 681090735-Bromo-1-diethoxymethyl-3-isopropyl-2-methoxybenzene

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

5-bromo-3-isopropyl-2-methoxybenzaldehyde (26.76 g) was dissolved in n-hexane (50 mL) and triethyl orthoformate (22 mL), and Amberlyst-15 (2.68 g) was added to the solution, and then the mixture was refluxed for 4 hours. The reaction solution was filtered, and then the solvent was distilled off under reduced pressure to obtain the title compound (31.55 g) as a brown oily substance.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. filtrationThe reaction solution was filtered
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1a3a8fff75674df485245040552b2319
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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