18-Pentatriacontanone → 18-Pentatriacontanol

HRID 434082Notes

Reaction equation

HRID 434082 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][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][CH2:23][C:24]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[O:25]>O1CCCC1>[OH:25][CH:24]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[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][CH2:8][CH3:7]

Participants

4

Reactant 2

HCID 1044018-PentatriacontanoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 28542418-Pentatriacontanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

18-Hydroxypentatriacontane (2-1) was prepared as follows and used without further purification. In a dry flask charged with argon was prepared a solution of lithium aluminum hydride (0.75 g, (19.8 mmol)) in freshly distilled tetrahydrofuran (400 mL). To this solution was added stearone (5.0 g, (9.9 mmol)). The reaction mixture was slowly brought to reflux (and allowed to stir at reflux overnight). After cooling to room temperature, the remaining lithium aluminum hydride was quenched by the dropwise addition of water (0.76 mL), followed by 15% NaOH (0.76 mL), and water again (2.2 mL). The reaction mixture was allowed to stir for 1 hour. The solvent was evaporated, and the resulting solids were triturated with hot toluene (300 mL). The toluene was evaporated to yield the desired alcohol (4.9 g. 97% yield) 1H NMR (300 MHz, CDCl3, TMS=0), δ3.58 (m, 1H), 1.38 (m, 4H), 1.25 (bs, 60H), 0.88 (t, 6H, J=6.5).

Workup

  1. customused without further purification
  2. additionIn a dry flask charged with argon
  3. temperatureto reflux
  4. customthe remaining lithium aluminum hydride was quenched by the dropwise addition of water (0.76 mL)
  5. stirringto stir for 1 hour
  6. customThe solvent was evaporated
  7. customthe resulting solids were triturated with hot toluene (300 mL)
  8. customThe toluene was evaporated

Sources & evidence

ORD record
ord-7322106ad31c4b689903c69abdc942d7
Source dataset
uspto-grants-2003_12
Patent number
US06670393B2

Reaction notes

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