Phosphorus oxide (P4O10) → 2-Methoxy-6,7,8,9-tetrahydro-benzocyclohepten-5-one

HRID 917483Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 917483
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[P].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=O)[CH:21]=[CH:22][CH:23]=1>>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]2[C:28](=[O:30])[CH2:27][CH2:26][CH2:25][CH2:24][C:20]=2[CH:19]=1

Komponenten

4

Edukt 3

HCID 14812Phosphorus oxide (P4O10)HCID 5462309PhosphorusHCID 105844855-(3-methoxyphenyl)pentanoic Acid

Produkt 1

HCID 2668152-Methoxy-6,7,8,9-tetrahydro-benzocyclohepten-5-oneAusbeute 95 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a homogeneous mixture of phosphorus pentoxide and 85% phosphorus acid at 100° C., was added 5-(3-methoxyphenyl)pentanoic acid in small portions over 20 minutes. The vigorously stirred mixture was heated at 100° C. for 6 hours. Then it was poured on ice-water, and extracted with ether (3 times). The organic phase was washed with water and dried over anhydrous sodium sulfate. Evaporation of the combined organic phase afforded a light yellow oil in more than 95% yield; 1H NMR δ 7.77 (d, 1H, J=8.6 Hz), 6.80 (dd, 1H, J=2.5, 8.6 Hz), 6.69 (d, 1H, J=2.5 Hz), 3.84 (s, 3H), 2.90 (t, 2H, J=6.2 Hz), 2.71 (t, 2H, J=5.9 Hz), 1.91-1.76 (m, 4H).

Aufarbeitung

  1. additionThen it was poured on ice-water
  2. extractionextracted with ether (3 times)
  3. washThe organic phase was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customEvaporation of the combined organic phase
  6. customafforded a light yellow oil in more than 95% yield

Quellen und Nachweise

ORD-Eintrag
ord-1effc4611c964a7c8f9a239644af0fda
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273880B2

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