Toluene → (3-Hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-methyl Triphenylphosphonium Bromide

HRID 2186550

Reaktionsgleichung

Reaktionsgleichung von HRID 2186550
[Br:1][CH2:2][C:3]1[C:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:11][C:10]2[C:9]([CH3:20])([CH3:19])[CH2:8][CH2:7][C:6]([CH3:22])([CH3:21])[C:5]=2[CH:4]=1.[C:23]1([P:29]([C:36]2C=CC=CC=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:42]1(C)[CH:47]=[CH:46]C=[CH:44][CH:43]=1>>[Br-:1].[CH2:2]([C:3]1[C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=2[P+:29]([CH3:36])([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:11][C:10]2[C:9]([CH3:20])([CH3:19])[CH2:8][CH2:7][C:6]([CH3:22])([CH3:21])[C:5]=2[CH:4]=1)[CH2:44][CH2:43][CH2:42][CH2:47][CH3:46]

Komponenten

4

Edukt 3

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 22456869HCID 22456869, Verbindung

Produkt 1

HCID 86758176(3-Hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-methyl Triphenylphosphonium Bromide

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

A solution of 2.58 g of 2-bromomethyl-3-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene (from Example 6) and 1.94 g of triphenylphosphine in 50 ml of toluene was heated to reflux (oil bath at 115° C.) for 3 hours. The mixture was cooled to −5° C. for 1 hour and the white solid was filtered off. Concentration in vacuo of the filtrate gave a pale yellow residue, which was crystallized from toluene. The combined white solids were dried, giving 4.0 g of the title product. 1H NMR (CDCL3): 7.78 (m, 3H), 7.50-7.75 (m, 12 H), 6.95 (s, 1H), 6.90 (s, 1H), 5.14 (d, J=15 Hz, 2H), 1.76 (t, J=7.8 Hz, 2 H), 1.50-1.70 (m, 4 H), 1.22 (s, 6 H), 1.30-1.05 (m, 8 H), 0.85 (t, J=6.8 Hz, 3 H), 0.81 (s, 6 H).

Aufarbeitung

  1. temperatureThe mixture was cooled to −5° C. for 1 hour
  2. filtrationthe white solid was filtered off
  3. concentrationConcentration in vacuo of the filtrate
  4. customgave a pale yellow residue, which
  5. customwas crystallized from toluene
  6. customThe combined white solids were dried

Quellen und Nachweise

ORD-Eintrag
ord-e66ab0204a304cd0926fff23831957da
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06403810B2

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