Sodium hydride → 4-Dodecyloxybenzyl(4-methoxymethyloxy-3-chlorophenyl) ether

HRID 1650644Notes

Reaction equation

HRID 1650644 reaction equation
[CH2:1]([O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH3:22][O:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][C:27]=1[Cl:33].[H-].[Na+]>CN(C)C=O>[CH2:1]([O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][C:28]2[C:27]([Cl:33])=[C:26]([O:25][CH2:24][O:23][CH3:22])[CH:31]=[CH:30][C:29]=2[O:32][C:29]2[CH:30]=[CH:31][C:26]([O:25][CH2:24][O:23][CH3:22])=[C:27]([Cl:33])[C:28]=2[CH2:18][C:17]2[CH:20]=[CH:21][C:14]([O:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:15][CH:16]=2)=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 222215803-Chloro-4-(methoxymethoxy)phenolHCID 230521791-(Bromomethyl)-4-(dodecyloxy)benzene

Product 1

HCID 571056214-Dodecyloxybenzyl(4-methoxymethyloxy-3-chlorophenyl) etherYield 58.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In dimethylformamide, 2 g of 4-dodecyloxybenzyl bromide synthesized in the same manner as described in Referential Example 17 was reacted with 1.5 g of 4-methoxymethyloxy-3-chlorophenol synthesized in the same manner as described in Example 11 in the presence of NaH to obtain 1.5 g of 4-dodecyloxybenzyl(4-methoxymethyloxy-3-chlorophenyl) ether. According to customary procedures, the methoxymethyl group was removed from the so-obtained compound in the presence of zinc in acetic acid to obtain 1.2 g of 4-dodecyloxybenzyl(4-hydroxy-3-chlorophenyl) ether.

Workup

  1. customsynthesized in the same manner

Sources & evidence

ORD record
ord-8a60b4385bf64dad8a53c453d3df97ef
Source dataset
uspto-grants-1990_05
Patent number
US04925591

Reaction notes

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