Ethanol → 4-(Diethoxymethyl)benzaldehyde

HRID 1968098Notes

Reaction equation

HRID 1968098 reaction equation
C(=O)[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(O)C.C(O[CH:17]([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])C>[Cl-].[NH4+]>[CH2:22]([O:21][CH:17]([O:18][CH2:19][CH3:20])[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH3:23]

Participants

5

Reactant 3

HCID 702EthanolHCID 12173TerephthalaldehydeHCID 31214Ethyl orthoformate

Product 1

HCID 5959934-(Diethoxymethyl)benzaldehydeYield 50%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideCatalyst

Procedure

A mixture of terephthalaldehyde (10 g, 74.55 mmol), ammonium chloride (160 mg, 3.0 mmol) in ethanol (10.3 g, 223.6 mmol) was added dropwise triethoxymethane (12.15 g, 82 mmol) at 0° C. After the addition, the mixture was stirred at room temperature overnight. The mixture was concentrated, the residue was purified by silica gel chromatography to give the title compound (7.0 g, yield 50%) as a white solid. LC-MS (ESI) m/z: 209 (M+1)+.

Workup

  1. additionAfter the addition
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-540c69af55ea4898a84b6d06475b95cb
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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