Ethanol → 3-(Diethoxymethyl)benzaldehyde

HRID 1968004Notes

Reaction equation

HRID 1968004 reaction equation
C(=O)[C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=1.C(O)C.[CH:14]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])OCC>[Cl-].[NH4+]>[CH2:22]([O:21][CH:14]([O:18][CH2:19][CH3:20])[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])[CH3:23]

Participants

5

Reactant 3

HCID 702EthanolHCID 31214Ethyl orthoformateHCID 34777Isophthalaldehyde

Product 1

HCID 162177103-(Diethoxymethyl)benzaldehydeYield 76%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideCatalyst

Conditions

Temperature
0 °C

Procedure

A mixture of isophthalaldehyde (21.44 g, 160 mmol), ammonium chloride (0.34 g, 6.38 mmol) in anhydrous ethanol (23.2 g, 480 mmol) was cooled to 0° C., then triethyl orthoformate was added drop-wise. After the addition, the mixture was warmed to 40° C. and stirred for two days. The mixture was filtered and the filtrate was concentrated to give crude product. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=200:1 to 100:1) to give 3-(diethoxymethyl)benzaldehyde (25.4 g, yield 76%) as a colorless oil. 1H-NMR (400 MHz, CDCl3) δ (ppm): 1.23-1.27 (m, 6H), 3.53-3.67 (m, 4H), 5.58 (s, 1H), 7.52-7.56 (t, J=7.6 Hz, 1H), 7.74-7.77 (dd, J1=7.6 Hz, J2=3.6 Hz, 1H), 8.00 (s, 1H), 10.04 (s, 1H); LC-MS (ESI) m/z: 209 (M+1)+.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was warmed to 40° C.
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. customto give crude product
  6. customThe crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=200:1 to 100:1)

Sources & evidence

ORD record
ord-9d99eedfd17e4b0ea878c0b72550a427
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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