Anisole → 18-(p-Iodophenyl)octadecanol

HRID 2228852Notes

Reaction equation

HRID 2228852 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 1165580418-(p-Iodophenyl)octadecanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-c862c67fc1314bc0b37fa46fea8c43bc
Source dataset
uspto-grants-2002_07
Patent number
US06417384B1

Reaction notes

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