Hydrochloric Acid → 2-Ethoxyphenol

HRID 2071709Notes

Reaction equation

HRID 2071709 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])[CH3:2].[OH-].[Na+].[CH2:13](Cl)[CH:14]=[CH2:15].[Cl-].[NH4+].Cl>O>[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([CH2:15][CH:14]=[CH2:13])[CH:7]=[CH:6][C:5]=1[OH:10])[CH3:2].[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])[CH3:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7850Allyl chlorideHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 667552-Ethoxyphenol

Product 2

HCID 667552-EthoxyphenolHCID 601250Ethyleugenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 11.60 g of o-ethoxyphenol, 3.36 g of sodium hydroxide, 7.07 g of allyl chloride, 1.37 g of cupric chloride (CuCl2.2H2O), 1.72 g of ammonium chloride and 34 ml of water was reacted at 25° C and with stirring, for 15 minutes. The reaction solution was then neutralized with hydrochloric acid and extracted with five portions of 30 ml of ether. The resulting ethereal extract was distilled to give 5.17 g of the desired o-ethoxy-p-allylphenol and 5.22 g of the unreacted o-ethoxyphenol. There was also obtained 2.02 g of by-product 1-allyloxy-2-ethoxybenzene.

Workup

  1. customwas reacted at 25° C
  2. extractionextracted with five portions of 30 ml of ether
  3. extractionThe resulting ethereal extract
  4. distillationwas distilled

Sources & evidence

ORD record
ord-452a04a1cb584f07add2a2edf4e3f482
Source dataset
uspto-grants-1977_09
Patent number
US04048236

Reaction notes

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