12-(3-Iodophenyl)dodecanoic acid → 12-m-Iodophenyldodecanol

HRID 482186Notes

Reaction equation

HRID 482186 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>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

3

Reactant 1

HCID 1458416312-(3-Iodophenyl)dodecanoic acid

Product 1

HCID 1458416412-m-IodophenyldodecanolYield 98.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Anhydrous THF (20 ml) was added to a flame-dried 100 ml two-necked flask containing 12-m-iodophenyldodecanoic acid (3.30 g, 8.21 mmol). The solution was cooled in an ice bath before BH3 -THF (15.0 ml, 1M) 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-8a076b725e4b4fda92d8a92fb133abad
Source dataset
uspto-grants-1998_08
Patent number
US05795561

Reaction notes

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