Toluene → 2,6,10-Trimethylundecan-1-ol

HRID 268409Notes

Reaction equation

HRID 268409 reaction equation
C1(C)C=CC=CC=1.[CH3:8][CH:9]([CH2:12][CH2:13][CH2:14][CH:15]([CH3:22])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH:10]=[O:11].[OH-].[Na+]>CCOCC>[CH3:8][CH:9]([CH2:12][CH2:13][CH2:14][CH:15]([CH3:22])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:10][OH:11]

Participants

5

Reactant 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 92737Undecanal, 2,6,10-trimethyl-

Product 1

HCID 125714642,6,10-Trimethylundecan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 70 ml. of 70% by weight of bis (2-methoxyethoxy) sodium aluminum hydride in toluene (0.25 mol) in 500 ml. of anhydrous diethyl ether was added, dropwise over 1.0 hour, 69.2 g. (0.326 mol.) of (±)-2,6,10-trimethylundecanal. The solution was stirred 1.0 hour, poured onto ice and 10N aqueous NaOH, and worked up with ether and dried as described in Example 2. Distillation of the crude product gave (±)-2,6,10-trimethylundecan-1-ol as a colorless oil; b.p. 96°-98°C./0.20 mmHg.

Workup

  1. customdried
  2. distillationDistillation of the crude product

Sources & evidence

ORD record
ord-cbb2adee340042baa58a6fe7c405c94a
Source dataset
uspto-grants-1976_03
Patent number
US03947473

Reaction notes

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