Hexamethylenetetramine → 5-Ethoxy-2-fluoro-4-hydroxy-benzaldehyde

HRID 1266698Notes

Reaction equation

HRID 1266698 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[OH:11])[CH3:2].C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:24](O)=[O:25]>>[CH2:1]([O:3][C:4]1[C:5]([OH:11])=[CH:6][C:7]([F:10])=[C:8]([CH:9]=1)[CH:24]=[O:25])[CH3:2]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acid2×HCID 185518382-Ethoxy-5-fluorophenol

Product 1

HCID 226475845-Ethoxy-2-fluoro-4-hydroxy-benzaldehyde

Conditions

Temperature
80 °C

Procedure

The 2-ethoxy-5-fluoro-phenol (14.3 g) described in example 1.2 was dissolved in trifluoroacetic acid (90 ml). This solution was slowly added to a solution of hexamethylene tetramine (25.7 g) in trifluoroacetic acid (90 ml) at 80° C. The mixture was stirred for 1 h at 80° C. and concentrated. Water (250 ml) was added and stirred for 10 min. The mixture was neutralized with Na2CO3 and extracted with ether. The crude product was purified by column chromatography (n-hexane/ethyl acetate) to yield 9.43 g of 5-ethoxy-2-fluoro-4-hydroxy-benzaldehyde as a yellow solid. MS: 184 ([M]+).

Workup

  1. concentrationconcentrated
  2. additionWater (250 ml) was added
  3. stirringstirred for 10 min
  4. extractionextracted with ether
  5. customThe crude product was purified by column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9156e57fd93c4e38b2adb931a31a39de
Source dataset
uspto-grants-2003_04
Patent number
US06548694B2

Reaction notes

Loading…