Borane;tetrahydrofuran → 12-m-Iodophenyldodecanol

HRID 1089343Notes

Reaction equation

HRID 1089343 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19](O)=[O:20])[CH:5]=[CH:6][CH:7]=1.B.C1COCC1>C1COCC1>[I:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 1458416312-(3-Iodophenyl)dodecanoic acid

Product 1

HCID 1458416412-m-IodophenyldodecanolYield 98.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Anhydrous THF (20 ml) was added to a flame-dried 100 ml two-necked flask contain 12-m-iodophenyldodecanoic acid (3.30 g, 8.21 mmol). The solution was cooled in an ice bath before BH3THF (15.0 ml, 1 M) was added dropwise. The reaction mixture was allowed to warm to room temperature and to stir under anhydrous conditions for 20 hours. The reaction mixture was again cooled to 0° C. and quenched with H2O. Ether and additional H2O were then added. The ether layer was extracted with H2O, sat. NaHCO3, and more H2O and dried (MgSO4). The solvent was removed under reduced pressure to yield a yellow oil. The crude compound was purified by column chromatography (90 g silica gel, hexanes:ethyl acetate 8:1) to yield a white solid, compound 8, 12-m-iodophenyldodecanol (3.14 g, 98.4% yield).

Workup

  1. additionwas added dropwise
  2. temperatureThe reaction mixture was again cooled to 0° C.
  3. customquenched with H2O
  4. additionEther and additional H2O were then added
  5. extractionThe ether layer was extracted with H2O, sat. NaHCO3, and more H2O
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed under reduced pressure
  8. customto yield a yellow oil
  9. customThe crude compound was purified by column chromatography (90 g silica gel, hexanes:ethyl acetate 8:1)

Sources & evidence

ORD record
ord-57dbb6ade9a64085ae12b88ea0a01f33
Source dataset
uspto-grants-1990_10
Patent number
US04965391

Reaction notes

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