Water → 4-Tetradecyloxybenzyl alcohol

HRID 235701

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([O-])=[O:27])=[CH:24][CH:23]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].O.[OH-].[Na+]>O1CCCC1>[CH2:7]([O:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:26][OH:27])=[CH:29][CH:30]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

Conditions

Temperature: 0 °C

Procedure

To about 13.61 g of lithium aluminum hydride in about 200 ml of tetrahydrofuran was added, over about 1/2 hour, a solution of about 130 g of 4-tetradecyloxybenzoate in about 400 ml of tetrahydrofuran, in an ice bath with stirring and maintaining the temperature below about 40° C. After stirring about 2 hours the mixture was cooled to about 0° C., about 9 ml of water was added dropwise followed by the dropwise addition of about 18 ml of about 15% sodium hydroxide and about 30 ml of water. This mixture was filtered through celite, the solvent was removed and the residue recrystallized from ethanol, giving about 94.5 g of the desired title compound as a white solid, mp 75°-76° C.

Workup

temperaturemaintaining the temperature below about 40° C
filtrationThis mixture was filtered through celite
customthe solvent was removed
customthe residue recrystallized from ethanol

Sources & evidence

ORD record: ord-ce3c53ea81fa4bcfab8cfcb2a31ca06c
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04640913

Linked notes

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