Formaldehyde → HCID 18008629, compound

HRID 987366Notes

Reaction equation

HRID 987366 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:7]=[CH:6][C:5]=1[OH:19])([CH3:3])[CH3:2].[CH3:20][O-:21].[Mg+2].C[O-].C=O>C1(C)C=CC=CC=1>[CH:1]([C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:7]=[C:6]([CH:20]=[O:21])[C:5]=1[OH:19])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 164537Methanol, magnesium salt (2:1)HCID 18008637HCID 18008637, compound

Product 1

HCID 18008629HCID 18008629, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

2-Isopropyl-4-nonylphenol (3a) (239.4 g, 0.914 mol) in toluene (470 mL) was placed in a 4-neck RBF equipped with a thermometer, a condenser, and a mechanical stirrer. To the solution was added methanolic magnesium methoxide (685 mL of 7.4 wt. %, d. 0.816 g/mL). The methanol was distilled off gradually so that the pot temperature was raised to 100° C. Then solid paraformaldehyde (80 g, 2.7 mol) was introduced in portions for 30 mins. maintaining the same temperature. Crude product was distilled and further purified by flash column chromatography to obtain 3-isopropyl-5-nonylsalicylaldehyde (52.6 g) in 20% yield.

Workup

  1. customequipped with a thermometer, a condenser, and a mechanical stirrer
  2. distillationThe methanol was distilled off gradually so that the pot temperature
  3. temperaturemaintaining the same temperature
  4. distillationCrude product was distilled
  5. customfurther purified by flash column chromatography

Sources & evidence

ORD record
ord-fbd99d61b09c4e8c8621f6ed1da402be
Source dataset
uspto-grants-2003_10
Patent number
US06632410B2

Reaction notes

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