Hydrochloric Acid → 2-Ethoxyphenol

HRID 2071708Notes

Reaction equation

HRID 2071708 reaction equation
[OH-].[Na+].[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])[CH3:4].[CH2:13](Cl)[CH:14]=[CH2:15].Cl>O>[CH2:3]([O:5][C:6]1[CH:11]=[C:10]([CH2:15][CH:14]=[CH2:13])[CH:9]=[CH:8][C:7]=1[OH:12])[CH3:4].[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])[CH3:4]

Participants

7

Reactant 4

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

Product 2

HCID 667552-EthoxyphenolHCID 601250Ethyleugenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 34 ml of water were added in order 3.36 g of sodium hydroxide, 11.60 g of o-ethoxyphenol, 0.716 g of cupric chloride (CuCl2.2H2O; catalyst) and 7.07 g of allyl chloride. The reaction took place at 83° C and with stirring, for 3 hours. 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 4.51 g of the desired o-ethoxy-p-allylphenol and 0.78 g of the unreacted o-ethoxyphenol. There was also obtained 6.56 g of by-product 1-allyloxy-2-ethoxybenzene.

Workup

  1. customat 83° C
  2. extractionextracted with five portions of 30 ml of ether
  3. extractionThe resulting ethereal extract
  4. distillationwas distilled

Sources & evidence

ORD record
ord-eac0ec537b37442292b1075a2dc7bb1d
Source dataset
uspto-grants-1977_09
Patent number
US04048236

Reaction notes

Loading…