Anisole → 18-(p-Iodophenyl)octadecanol

HRID 1383870Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1383870
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([I:33])=[CH:29][CH:28]=1)C1C=CC=CC=1.C1(OC)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[I:33][C:30]1[CH:29]=[CH:28][C:27]([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][OH:8])=[CH:32][CH:31]=1

Komponenten

5

Edukt 3

HCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 184715971-Benzyloxy-18-(p-iodophenyl)octadecane2×

Produkt 1

HCID 1165580418-(p-Iodophenyl)octadecanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Finally, to a solution of 1-benzyloxy-18-(p-iodophenyl)octadecane (Compound V) (185 mg; 0.33 mmol) and anisole (0.15 ml; 1.32 mmol) in dichloromethane (3 ml) was added anhydrous aluminum chloride (135 mg; 1 mmol) at the room temperature. Stirring was continued for 2 h. The reaction was quenched by diluted hydrochloric acid and extracted by chloroform. Extract was dried (Na2SO4) and evaporated. The residue was chromatographed in hexane-ethyl acetate (gradient from 95:5 to 85:15) to give 18-(p-iodophenyl) octadecanol, Compound VI (123 mg; 77%).

Aufarbeitung

  1. customThe reaction was quenched by diluted hydrochloric acid
  2. extractionextracted by chloroform
  3. extractionExtract
  4. dry with materialwas dried (Na2SO4)
  5. customevaporated
  6. customThe residue was chromatographed in hexane-ethyl acetate (gradient from 95:5 to 85:15)

Quellen und Nachweise

ORD-Eintrag
ord-54e0b1ce383743008d3153e25f6a14f2
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255519B1

Notizen zur Reaktion

Wird geladen…