Chlorohydroquinone → 4-Dodecyloxybenzyl(4-hydroxy-2-chlorophenyl) ether

HRID 1650645Notes

Reaction equation

HRID 1650645 reaction equation
[OH-:1].[Na+].[CH2:3]([O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[OH:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][C:26]=1[Cl:32].[ClH:33]>>[CH2:3]([O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][C:16]2[C:17]([Cl:33])=[C:18]([O:24][C:25]3[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([CH2:20][C:19]4[CH:22]=[CH:23][C:16]([O:15][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:17][CH:18]=4)[C:26]=3[Cl:32])[CH:19]=[CH:22][C:23]=2[OH:1])=[CH:18][CH:17]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 4

HCID 301ChlorohydroquinoneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 230521791-(Bromomethyl)-4-(dodecyloxy)benzene

Product 1

HCID 569758784-Dodecyloxybenzyl(4-hydroxy-2-chlorophenyl) ether

Procedure

In an aqueous solution of sodium hydroxide, 2.0 g of 4-dodecyloxybenzyl bromide synthesized in the same manner as described in Referential Example 17 was reacted under reflux with 1.0 g of 4-hydroxy-3-chlorophenol for 8 hours, the thus-obtained solution was put into ice-cooled hydrochloric acid, and the precipitate was recovered by filtration, washed, dried and purified by the silica gel column chromatography to obtain 0.8 g of 4-dodecyloxybenzyl(4-hydroxy-2-chlorophenyl) ether.

Workup

  1. customwas reacted
  2. filtrationthe precipitate was recovered by filtration
  3. washwashed
  4. customdried
  5. custompurified by the silica gel column chromatography

Sources & evidence

ORD record
ord-01eaf141db0c4242a015161c5ff95c91
Source dataset
uspto-grants-1990_05
Patent number
US04925591

Reaction notes

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