Hexamethylenetetramine → 3,5-Difluoro-4-hydroxybenzaldehyde
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[OH:9].C1N2CN3CN(C2)CN1C3.[C:20](O)(C(F)(F)F)=[O:21]>>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([F:8])[C:3]=1[OH:9])[CH:20]=[O:21]Participants
4
Conditions
- Temperature
- 130 °C
Procedure
To a solution of 2,6-difluoro phenol (1 g; 7.69 mmol) in CF3COOH (10 ml) is added hexamethylene tetramine (1.08 g; 7.69 mmol) and the mixture is heated in a microwave apparatus at 130° C. for 15 min. After evaporation to dryness the residue is taken-up in CH2Cl2 and saturated K2CO3 solution. After acidification with hydrochloric acid the aqueous layer is extracted with CH2Cl2 (3×100 ml). The combined organic layer is washed with brine, dried over MgSO4 and evaporated to dryness to give 3,5-difluoro-4-hydroxy-benzaldehyde as a colourless solid (0.82 g).
Workup
- customAfter evaporation to dryness the residue
- extractionAfter acidification with hydrochloric acid the aqueous layer is extracted with CH2Cl2 (3×100 ml)
- washThe combined organic layer is washed with brine
- dry with materialdried over MgSO4
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-ce4f8537e0d44409abea1befc5fd7b62
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07714010B2
Reaction notes
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