Sodium Hydroxide → 2-(Prop-2-en-1-yloxy)propanoic acid

HRID 542610Notes

Reaction equation

HRID 542610 reaction equation
C([O:3][C:4](=[O:11])[CH:5]([O:7][CH2:8][CH:9]=[CH2:10])[CH3:6])C.[OH-].[Na+]>O>[CH2:8]([O:7][CH:5]([CH3:6])[C:4]([OH:11])=[O:3])[CH:9]=[CH2:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 535120Ethyl 2-(allyloxy)propanoate

Product 1

HCID 112288112-(Prop-2-en-1-yloxy)propanoic acidYield 79.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Allyloxypropionic acid ethyl ester (147.2 g, 0.93 mol), water (300 ml) and NaOH (44.7 g) were fed into a flask, followed by agitating the mixture for about 5 to 6 hours while the reaction temperature was kept at about 60° C., thereafter dropwise adding conc. hydrochloric acid (90 ml) under ice cooling, extracting the resulting deposited oily substance with isopropyl ether, drying over MgSO4 and carrying out vacuum distillation to obtain 2-allyloxypropionic acid (95.7 g, 108° C./5 mmHg). Yield: 79%.

Workup

  1. customwas kept at about 60° C.
  2. extractiondropwise adding conc. hydrochloric acid (90 ml) under ice cooling, extracting the resulting deposited oily substance with isopropyl ether
  3. dry with materialdrying over MgSO4
  4. distillationvacuum distillation

Sources & evidence

ORD record
ord-56a87af2653e42c28a873e7bf659bb3e
Source dataset
uspto-grants-1987_04
Patent number
US04658049

Reaction notes

Loading…