Hydrochloric Acid → 4-(4-Ethoxyphenoxy)-2-isopropylphenyl benzyl ether

HRID 260788

Reaction equation

HRID 260788 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][C:10]=1[CH:16]([CH3:18])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([O:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[CH3:20].C(=O)([O-])[O-].[K+].[K+].Cl>[Cu].N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:28][C:25]2[CH:26]=[CH:27][C:22]([O:21][CH2:19][CH3:20])=[CH:23][CH:24]=2)=[CH:11][C:10]=1[CH:16]([CH3:18])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 121504-EthoxyphenolHCID 214663451-(Benzyloxy)-4-bromo-2-isopropylbenzene

Product 1

HCID 214662534-(4-Ethoxyphenoxy)-2-isopropylphenyl benzyl etherYield 37.1%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 10 g of 4-bromo-2-isopropylphenyl benzyl ether, 4.7 g of 4-ethoxyphenol, 4.7 g of potassium carbonate, 0.30 g of copper powder, 0.30 g of cuprous iodide and 30 ml of pyridine was stirred at 130° C. to 140° C. for 24 hours. The reaction solution was cooled to room temperature, poured into ice-water and then acidified by adding 10% hydrochloric acid. The solution was extracted with 100 ml of diethyl ether, washed in turn with 10% hydrochloric acid, an aqueous 10% sodium hydroxide solution and a saturated saline solution, dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography to give 4.4 g of 4-(4-ethoxyphenoxy)-2-isopropylphenyl benzyl ether (yield, 37%).

Workup

  1. extractionThe solution was extracted with 100 ml of diethyl ether
  2. washwashed in turn with 10% hydrochloric acid
  3. dry with materialan aqueous 10% sodium hydroxide solution and a saturated saline solution, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e61f5b7aa21e4424b337909c81d83b33
Source dataset
uspto-grants-1996_06
Patent number
US05530015

Linked notes

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