Ethanol → 4-(Diethoxymethyl)benzaldehyde

HRID 1467718Notes

Reaction equation

HRID 1467718 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-37cc4082b27c48758d00be673bc04beb
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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