Phosphorus oxychloride → HCID 368833, compound

HRID 1647314Notes

Reaction equation

HRID 1647314 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH2:13][C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=2)[C:10]([OH:12])=O)=[CH:5][CH:4]=1.P(Cl)(Cl)(Cl)=O>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:10](=[O:12])[C:19]3[C:14](=[CH:15][C:16]([O:24][CH3:25])=[C:17]([O:22][CH3:23])[C:18]=3[O:20][CH3:21])[CH2:13]2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 368835HCID 368835, compound

Product 1

HCID 368833HCID 368833, compound

Procedure

A solution of the acid 33 (0.5 g, 1.4 mmol) in phosphorous oxychloride (5 mL, 53.4 mmol) was heated at reflux for 3 min. The dark red solution was poured onto crushed ice (about 30 g) and extracted with ether (50, 20, and 20 mL). The combined ether layer was dried over anhydrous sodium sulfate. Evaporation of the filtrate gave a gray solid. Recrystallization of this gray solid from ethyl acetate and hexane afforded pale gray crystals 0.32 g (69.6%): mp 104°-106° C.; IR (KBr) 3010, 2960, 1697, 1595, 1512, 1323, 1251, 1139 cm-1 ; 1H NMR (CDCl3, 200 MHz) δ7.11 (d, 2H, J=8 Hz), 6.85 (d, 2H, J=8 Hz), 6.71 (s, 1H), 4.03 (s, 3H), 3.96 (s, 3H), 3.87 (s, 3H), 3.78 (s, 3H), 3.78 (m, 1H), 3.54 (m, 1 H), 3.10 (m, 1H); EIMS m/e 328 (M+, 98). Anal. (C19H20O5), C, H.

Workup

  1. temperatureat reflux for 3 min
  2. additionThe dark red solution was poured
  3. extractionextracted with ether (50, 20, and 20 mL)
  4. dry with materialThe combined ether layer was dried over anhydrous sodium sulfate
  5. customEvaporation of the filtrate
  6. customgave a gray solid
  7. customRecrystallization of this gray solid from ethyl acetate and hexane afforded pale gray crystals 0.32 g (69.6%)

Sources & evidence

ORD record
ord-598eae88f84544af82ad29e68d1d73eb
Source dataset
uspto-grants-1995_07
Patent number
US05430062

Reaction notes

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