Ethanol → 4-(Diethoxymethyl)benzaldehyde

HRID 907980Notes

Reaction equation

HRID 907980 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-1448eee1f6f445d4ab99dbdd82808a88
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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