Methanol → 18-(p-Iodophenyl)octadecanol

HRID 910818Notes

Reaction equation

HRID 910818 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][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][C:23]1[CH:28]=[CH:27][C:26]([I:29])=[CH:25][CH:24]=1)(=O)C.CO.[OH-].[Na+]>C1COCC1.O>[I:29][C:26]1[CH:25]=[CH:24][C: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][CH2:8][CH2:7][CH2:6][CH2:5][OH:4])=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 5754870918-(p-Iodophenyl)octadecyl acetate

Product 1

HCID 1165580418-(p-Iodophenyl)octadecanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

18-(p-Iodophenyl)octadecyl acetate 42 (1.55 g, 3.01 mmol) was dissolved in THF (10 ml), MeOH (5 ml) and solution of NaOH (240 mg, 6.03 mmol) in H2O (1 ml) was added. The reaction mixture was stirred at room temperature for 2 h, quenched with aqueous NaHCO3 solution and extracted with EtOAc. Extract was dried over Na2SO4 and evaporated. Silica gel chromatography in hexane-EtOAc (95:5, 90:10) gave the product, 1.36 g (95%).

Workup

  1. customquenched with aqueous NaHCO3 solution
  2. extractionextracted with EtOAc
  3. extractionExtract
  4. dry with materialwas dried over Na2SO4
  5. customevaporated
  6. customSilica gel chromatography in hexane-EtOAc (95:5, 90:10) gave the product, 1.36 g (95%)

Sources & evidence

ORD record
ord-e629915b9c3a4bbb88b56419d8909466
Source dataset
uspto-grants-2011_09
Patent number
US08022235B2

Reaction notes

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