Phosphoric Acid → 4,4-Dimethylthiochroman

HRID 1110981Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1110981
[CH3:1][C:2](O)([CH2:4][CH2:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:3].OP(O)(O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>[Na]>[CH3:1][C:2]1([CH3:3])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[S:6][CH2:5][CH2:4]1

Komponenten

5

Edukt 3

HCID 1004Phosphoric AcidHCID 14812Phosphorus oxide (P4O10)HCID 144422552-Methyl-4-(phenylthio)-2-butanol

Produkt 1

HCID 110194304,4-DimethylthiochromanAusbeute 86,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5360545SodiumLösungsmittel

Versuchsvorschrift

A mixture of 15.00 grams (0.076 mol) of 2-methyl-4-(phenylthio)-2-butanol, 12.75 grams of H3PO4, 27.0 grams (0.190 mol) of P2O5 [this is added in three equal portions every 8 h] and 60 mL of sodium-dried benzene was boiled under N2 for 24 hours in a 250-mL, round-bottom flask equipped with a condenser and nitrogen inlet. The resulting, cooled heterogeneous mixture was separated and the P2O5 layer was extracted with ether. The combined organic layers were washed with H2O, brine, dried with Na2SO4 (4 h). Evaporation and vacuum distillation gave 11.68 grams (86.0%) of 4,4-dimethylthiochroman as a clear colorless liquid: bp 75°-82° C./0.1 mm; 1H NMR (DCCl3) δ1.29 [s, 6H, (CH3)2C] 1.92 [m, 2H, ArSCH2CH2 ] 3.00 [m, 2H, ArSCH2CH2 ] 6.90-7.32 [m, 4H, Ar--H]; 13C NMR (DCCl3) ppm 22.8 [ArSCH2CH2 ], 29.9 [(CH3)2C] 32.6 [(CH3)C], 37.4 [ArSCH2CH2 ], 123.7, 125.7, 126.1, 126.2, 131.5, 141.5. ##STR13##

Aufarbeitung

  1. customequipped with a condenser and nitrogen inlet
  2. temperatureThe resulting, cooled heterogeneous mixture
  3. customwas separated
  4. extractionthe P2O5 layer was extracted with ether
  5. washThe combined organic layers were washed with H2O, brine
  6. dry with materialdried with Na2SO4 (4 h)
  7. customEvaporation and vacuum distillation

Quellen und Nachweise

ORD-Eintrag
ord-b25909f98236466fa53d3efc37c606f3
Quelldatensatz
uspto-grants-1990_12
Patentnummer
US04977276

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