Hexamethylenetetramine → HCID 19575787, compound

HRID 1862611Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH3:16])=[C:6]([CH:14]=1)[O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].C1N2CN3CN(C2)CN1C3.[C:27](=O)(O)[O-:28].[Na+]>FC(F)(F)C(O)=O>[Cl:1][C:2]1[C:3]([CH:27]=[O:28])=[CH:4][C:5]([O:15][CH3:16])=[C:6]([CH:14]=1)[O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of ethyl 2-(5-chloro-2-methoxy-phenoxy)acetate (606 mg) in trifluoroacetic acid (12 ml) was added hexamethylenetetramine (382 mg) at room temperature, and the mixture was stirred for 9 hours at 60° C. After concentration of the reaction mixture under reduced pressure, a saturated aqueous sodium bicarbonate solution was added to the residue, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. After the solvent was removed under reduced pressure, purification of the residue by flash column chromatography on silica gel (eluent: hexane/ethyl acetate=6/1) gave ethyl 2-(5-chloro-4-formyl-2-methoxyphenoxy)acetate (354 mg).

Workup

extractionthe resulting mixture was extracted with ethyl acetate
washThe extract was washed with water
dry with materialdried over anhydrous magnesium sulfate
customAfter the solvent was removed under reduced pressure, purification of the residue by flash column chromatography on silica gel (eluent: hexane/ethyl acetate=6/1)

Sources & evidence

ORD record: ord-8eea02d380d6405480b7227e8b310ffe
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06538152B1

Reaction notes

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