Phenol → 4,4-Dimethylchroman

HRID 862256

Reaktionsgleichung

Reaktionsgleichung von HRID 862256
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P([O-])([O-])(O[CH2:11][C:12](C1C=CC=CC=1)([C:16]1C=CC=CC=1)[C:13](C)=[CH2:14])=O>C(=S)=S>[CH3:11][C:12]1([CH3:16])[C:6]2[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=2)[O:7][CH2:14][CH2:13]1

Komponenten

4

Edukt 2

HCID 996PhenolHCID 131715882Diphenyl-3-methyl-3-buten-1-yl phosphate2×

Produkt 1

HCID 3167634,4-Dimethylchroman

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6348Carbon DisulfideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a dry, ice-cooled flask containing 34.95 g (0.134 mol) of stannic chloride was added quickly under argon 63.0 g (0.669 mol) of phenol. The mixture was stirred at 0 degrees C for 0.5 hour and then treated with 43.0 g (0.135 mol) of diphenyl-3-methyl-3-buten-1-yl phosphate (Compound 75), followed by a 5 ml carbon disulfide rinse. The mixture was stirred at room temperature for 21 hours and then quenched by pouring onto 700 g ice and 1 liter of 1.5N NaOH. The mixture was extracted with 1×600 ml and 2×300 ml ether. The combined ether fractions were washed with 2N NaOH, saturated NaCl and dried (MgSO4). Solvent was removed in vacuo and the residue purified by flash chromatography (silica; 2% ether in hexane) to give the title compound as a colorless oil. PMR (CDCl3) &: 1.34 (6H), 1.80-1.85 (2H, m), 4.15-4.20 (2H, m), 6.80 (1H, dd, J~8.1 hz, 1.5 Hz), 6.87 (1H, td, J~8.1 Hz, 1.5 Hz), 7.07 (1H, td, J~8.1 Hz, 1.5 Hz), 7.26 (1H, dd, J~8.1 Hz, 1.5 H).

Aufarbeitung

  1. temperatureTo a dry, ice-cooled flask
  2. washrinse
  3. stirringThe mixture was stirred at room temperature for 21 hours
  4. customquenched
  5. additionby pouring onto 700 g ice and 1 liter of 1.5N NaOH
  6. extractionThe mixture was extracted with 1×600 ml and 2×300 ml ether
  7. washThe combined ether fractions were washed with 2N NaOH, saturated NaCl
  8. dry with materialdried (MgSO4)
  9. customSolvent was removed in vacuo
  10. customthe residue purified by flash chromatography (silica; 2% ether in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0972cf8338004bf194b257aacc4a6a8b
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05717094

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