Methyl 4-(tetradecyloxy)benzoate → 4-Tetradecyloxybenzyl alcohol

HRID 247929

Reaction equation

HRID 247929 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:12][CH:11]=1>O1CCCC1>[CH2:17]([O:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][OH:8])=[CH:15][CH:14]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 3312490Methyl 4-(tetradecyloxy)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 100873844-Tetradecyloxybenzyl alcoholYield 97.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a room temperature solution of 3.27 g lithium aluminum hydride in 80 ml of dry tetrahydrofuran is added, dropwise, 10 g of product from Example 1 in 70 ml of dry tetrahydrofuran. The reaction is stirred at room temperature for 51/2 hours, quenched with a saturated sodium sulfate solution, filtered and the filtrate concentrated in vacuo. The residue is purified by column chromatography (silica gel:20% ethyl acetate/hexane) to give 9.0 g of desired product as colorless needles.

Workup

  1. customquenched with a saturated sodium sulfate solution
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue is purified by column chromatography (silica gel:20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3eea211d9f8044c0aca76339ea54b198
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Linked notes

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