Formaldehyde → 4-Hydroxy-2,3,5-trimethylbenzaldehyde

HRID 85010

Reaction equation

C1N2CN3CN(C2)CN1C3.C=O.[C:13]([O-])(=[O:15])C.[NH4+].[CH3:18][C:19]1[C:24]([CH3:25])=[CH:23][CH:22]=[C:21]([CH3:26])[C:20]=1[OH:27]>C(O)(=O)C>[CH3:25][C:24]1[C:19]([CH3:18])=[C:20]([OH:27])[C:21]([CH3:26])=[CH:22][C:23]=1[CH:13]=[O:15]

Participants

Conditions

Temperature: 120 °C

Procedure

Instead of hexamethylenetetramine as applied in Example 2A and 2B, formaldehyde and ammonium acetate in acetic acid were used for formylation as illustrated below. A 250 ml three neck round bottom flask equipped with a reflux condenser was charged with 20.4 g (0.15 mol) of 2,3,6-trimethylphenol. 100 ml acetic acid, 3.09 g (0.04 mol) of ammonium acetate and 3.243 g (0.04 mol) of formalin solution were added to it. The reaction mass was heated at 120° C. over a period of 2.5 hrs. The completion of reaction was confirmed by TLC. The reaction mass was poured into 400 ml ice cold water with stirring. The solid was filtered and washed with 2×50 ml process water. The product was dried under vacuum to afford 17 g (75%) of crude 2,3,5-trimethyl-4-hydroxy-benzaldehyde. The purification of crude product with 1% sodium hydroxide solution afforded 13 g (53%) of pure 2,3,5-trimethyl-4-hydroxyl-benzaldehyde.

Workup

customThe completion of reaction
filtrationThe solid was filtered
washwashed with 2×50 ml process water
customThe product was dried under vacuum

Sources & evidence

ORD record: ord-05837208b17746a08c42c30a85c05bfd
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846982B2

Linked notes

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