Toluene → Butyl 2-(4-hydroxyphenoxy)propanoate

HRID 485840Notes

Reaction equation

HRID 485840 reaction equation
C([C:3]1[CH:18]=[CH:17][C:6]([O:7][CH:8]([CH3:16])[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:10])=[CH:5][CH:4]=1)=O.C1(C)C=CC=CC=1.C(OO)(=[O:28])C>O>[OH:28][C:3]1[CH:18]=[CH:17][C:6]([O:7][CH:8]([CH3:16])[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6585Peracetic AcidHCID 13563056Butyl 2-(4-formylphenoxy)propionate

Product 1

HCID 12919928Butyl 2-(4-hydroxyphenoxy)propanoateYield 81.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

While stirring a mixture of 25 g of butyl 2-(4-formylphenoxy)propionate and 75 g of toluene at room temperature, 22.8 g of 40% peracetic acid was dropwise added. After stirring at 20° to 30° C. for 2 hours and at 50° C. for 2 hours, 2.0 g of water was added, and the mixture was stirred for 2 hours. The reaction mixture was cooled to room temperature and subjected to the same after-treatment as in Example 1, whereby 19.5 g of butyl 2-(4-hydroxyphenoxy)propionate was obtained as a colorless transparent liquid by the distillation under reduced pressure. The boiling point was 160° C./1 mmHg.

Workup

  1. stirringAfter stirring at 20° to 30° C. for 2 hours and at 50° C. for 2 hours
  2. stirringthe mixture was stirred for 2 hours

Sources & evidence

ORD record
ord-6a0b93ca6756416da6df04a6a83e6c27
Source dataset
uspto-grants-1985_08
Patent number
US04537984

Reaction notes

Loading…