Phenol → Benzenemethanol, 3-phenoxy-, 1-acetate

HRID 247721Notes

Reaction equation

HRID 247721 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[C:10]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17](Br)[CH:16]=1)(=[O:12])[CH3:11]>C1(C)C(C)=CC=CC=1>[C:10]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:16]=1)(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 996PhenolHCID 14797Potassium HydroxideHCID 12858554Benzenemethanol, 3-bromo-, 1-acetate

Product 1

HCID 170904Benzenemethanol, 3-phenoxy-, 1-acetateYield 77%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

10.35 g. (0.11 mole) of phenol, 6.15 g. (0.11 mole) of potassium hydroxide and 35 cm3. of xylene are weighed together. The water is azeotropically distilled with stirring and boiling. 5 cm3. of pyridine and 0.5 g. of copper(I) chloride are added then 22.91 g. (0.1 mole) of 3-bromobenzyl acetate are dropped into the reaction mixture during 15 minutes with stirring and boiling. The reaction mixture is boiled with stirring for an additional three hours. After cooling the reaction mixture is filtered off and the filtrate washed with a mixture of 25 cm3. of 15% sodium chloride solution and 2 cm3. of 40% sodium hydroxide solution. The organic phase is evaporated in vacuo. The residue is distilled in vacuo and so 18.65 g. of 3-phenoxybenzyl acetate are obtained. Boiling point 142°-145° C./53.2 Pa, nD20 : 1.5621, yield 77%.

Workup

  1. distillationThe water is azeotropically distilled
  2. additionof copper(I) chloride are added
  3. stirringwith stirring
  4. stirringwith stirring for an additional three hours
  5. temperatureAfter cooling the reaction mixture
  6. filtrationis filtered off
  7. washthe filtrate washed with a mixture of 25 cm3
  8. customThe organic phase is evaporated in vacuo
  9. distillationThe residue is distilled in vacuo and so 18.65 g

Sources & evidence

ORD record
ord-9324d319bedd4b14a18344d4054d26d2
Source dataset
uspto-grants-1987_11
Patent number
US04709081

Reaction notes

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