Trifluoroacetic acid → HCID 14838646, compound

HRID 1681857Notes

Reaction equation

HRID 1681857 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:12]1[C:13]([OH:22])=[C:14]([CH2:19][CH:20]=O)[CH:15]=[C:16]([Cl:18])[CH:17]=1)([O:10][CH3:11])=[O:9]>>[C:8]([C:12]1[C:13]2[O:22][CH:20]=[CH:19][C:14]=2[CH:15]=[C:16]([Cl:18])[CH:17]=1)([O:10][CH3:11])=[O:9]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 14838645HCID 14838645, compound

Product 1

HCID 14838646HCID 14838646, compoundYield 63.2%

Procedure

A trifluoroacetic acid (25 ml) solution of 3-carbomethoxy-5-chloro-2-hydroxyphenylacetaldehyde (5c) (5.20 g, 22.7 mmol) was refluxed for 2 hours under argon, and then poured into saturated Na2CO3The resulting precipitate was collected by filtration, and then purified by column chromatography (100% CH2Cl2) to give 6c as a cream colored solid (3.02 g, 63.2% yield). Analytical sample was prepared by recrystallization from ethyl ether, mp 144°-145° C. IR (nujol) 1710 (ester) cm-1. NMR (CDCl3) δ7.87-6.70 (m, 4H, aromatic protons) and 4.0 (s, 3H, CH3).

Workup

  1. additionpoured into saturated Na2CO3The resulting precipitate
  2. filtrationwas collected by filtration
  3. custompurified by column chromatography (100% CH2Cl2)

Sources & evidence

ORD record
ord-43eb209c516241d18489602bcee9fc2c
Source dataset
uspto-grants-1992_12
Patent number
US05175173

Reaction notes

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