1-Chloromethylnaphthalene → (1-Naphthylmethyl)triphenylphosphonium chloride

HRID 845224Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 845224
[Cl:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O>[Cl-:1].[C:3]1([CH2:2][P+:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 68451-ChloromethylnaphthaleneHCID 11776Triphenylphosphine

Produkt 1

HCID 2734113(1-Naphthylmethyl)triphenylphosphonium chlorideAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 5.3 g (0.03 mole) of 1-(chloromethyl)naphthalene and 8.6556 g (0.033 mole) of triphenylphosphine in 150 mL of dimethylformamide was heated at reflux with stirring for 5 hours. A copious white precipitate formed. The precipitate was filtered and washed with 100 mL of dimethylformamide and 100 mL of ether. The product was dried in vacuo to yield 11.97 g (91%) of 1-naphthylmethyltriphenylphosphonium chloride as white crystals: mp 285°-288°; IR (KBr) 3050, 3010, 2880, 2790, 1665, 1590, 1510, 1485, 1440, 1385, 1335, 1275, 1155, 1110, 1095, 875, 810, 785, 730, and 690 cm-1 ; NMR (DMSO) δ5.67 (d, J=15 Hz, 2H), 7.60 (m, 15H) and 7.73 (m, 7H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux
  3. customA copious white precipitate formed
  4. filtrationThe precipitate was filtered
  5. washwashed with 100 mL of dimethylformamide and 100 mL of ether
  6. customThe product was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c9a94c6f32974d75a254738c4b4625b5
Quelldatensatz
uspto-grants-1988_07
Patentnummer
US04757079

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