HCID 58697787, compound → HCID 58697786, compound

HRID 2213571Notes

Reaction equation

HRID 2213571 reaction equation
[C:1]1([C@H:7]([O:12][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=2[O:21]CC2C=CC(OC)=CC=2)[CH:16]=[O:17])[C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C>[C:1]1([C@H:7]([O:12][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=2[OH:21])[CH:16]=[O:17])[C:8]([F:11])([F:10])[F:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 58697787HCID 58697787, compound

Product 1

HCID 58697786HCID 58697786, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-[(S)-1-phenyl-2,2,2-trifluoroethoxy]-4-[(4-methoxyphenyl)methoxy]-benzaldehyde (2.08 g, 0.005 mol) in acetic acid (25 mL) was heated to 150□C. and stirred for 72 h. It was then cooled to room temperature and concentrated in vacuo. The residue was diluted with ethyl acetate (100 mL), and the organic solution washed with water (100 mL) and extracted with 1M sodium hydroxide (5×100 mL). The basic extracts were combined and acidified to pH 1 with concentrated HCl, then extracted with ethyl acetate (2×100 mL). The organic extracts were combined, dried over sodium sulfate and evaporated. The residue was purified by chromatography on silica gel and elution with petroleum ether:ethyl acetate (6:1) gave the product as a colourless oil, which later crystallised to a white powder (1.14 g, 80%). RF (dichloromethane) 0.53. 1H NMR (CDCl3) □ 9.71 (s, 1H, O═C—H), 7.09 (d, 1H, J 8.3 Hz, ArH), 6.39 (s, 1H, OH), 5.50 (q, 1H, J 6.0 Hz, CHCF3).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with ethyl acetate (100 mL)
  3. washthe organic solution washed with water (100 mL)
  4. extractionextracted with 1M sodium hydroxide (5×100 mL)
  5. extractionextracted with ethyl acetate (2×100 mL)
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue was purified by chromatography on silica gel and elution with petroleum ether:ethyl acetate (6:1)

Sources & evidence

ORD record
ord-b995a8c975634f8383facb90eb51ad8b
Source dataset
uspto-grants-2006_09
Patent number
US07105554B2

Reaction notes

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