Methanol → Benzenedodecanol, 4-iodo-

HRID 1367715Notes

Reaction equation

HRID 1367715 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][C:17]1[CH:22]=[CH:21][C:20]([I:23])=[CH:19][CH:18]=1)(=O)C.CO.[OH-].[Na+]>C1COCC1.O>[I:23][C:20]1[CH:19]=[CH:18][C: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:22][CH:21]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 57548716HCID 57548716, compound

Product 1

HCID 11718029Benzenedodecanol, 4-iodo-Yield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

12-(p-Iodophenyl)dodecyl acetate 34 (872 mg, 2.03 mol) was dissolved in THF (4 ml) and MeOH (4 ml) mixture, and a solution of NaOH (325 mg, 8.11 mmol) in H2O (1 ml) was added. The mixture was stirred at room temperature for 5 h, quenched with 1 N HCl to pH 7, diluted with NaHCO3 solution and extracted with EtOAc. The extract was dried over Na2SO4 and the solvent was evaporated. Silica gel chromatography of the residue in hexane-ethyl acetate (95:5, 90:10) yielded the product (682 mg, 87%) as a white solid.

Workup

  1. customquenched with 1 N HCl to pH 7
  2. additiondiluted with NaHCO3 solution
  3. extractionextracted with EtOAc
  4. dry with materialThe extract was dried over Na2SO4
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-73321826ca2c46f2a6623ee7bcb7f4b4
Source dataset
uspto-grants-2011_02
Patent number
US07893286B2

Reaction notes

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