Benzyloxyacetic acid

Chemical Properties

Colorless liquid

Uses

Benzyloxyacetic acid may be used for the following syntheses:

• mixed benzyloxyacetic pivalic anhydride
• chiral glycolates, 1,2:4,5-di-O-isopropylidene-β-D-fructopyranos-3-yl benzyloxyacetate, via esterification
• tetraaqua(1,10-phenanthroline-[κ]²N,N′)magnesium(II) bis[(2,4-dichlorophenyl)acetate]
• as ligand in the preparation of diaquabis(benzyloxyacetato)copper(II) complex

Uses

It is a compound for proteomics research use. It may be used for following synthesis mixed benzyloxyacetic pivalic anhydride, chiral glycolates, 1,2:4,5-di-O-isopropylidene-β-D-fructopyranos-3-yl benzyloxyacetate, via esterification, tetra aqua(1,10-phenanthroline-[κ]2N,N?)magnesium(II) bis[(2,4-dichlorophenyl)acetate], as ligand in the preparation of diaquabis(benzyloxyacetato)copper(II) complex.

Definition

ChEBI: (benzyloxy)acetic acid is a monocarboxylic acid that is benzyl alcohol in which the hydroxy group is replaced by a carboxymethoxy group. It is a monocarboxylic acid, an ether and a member of benzenes. It is functionally related to a benzyl alcohol and a glycolic acid.

General Description

In vitro activities of phenoxy and benzyloxyacetic acid derivatives as antisickling agents has been investigated by the application of quantitative structure activity relationship (QSAR) of Hansch-type.

Synthesis

79-11-8

100-51-6

30379-55-6

1. 960 g of tetrahydrofuran and 41 g of toluene were added to the reaction flask. 2. 534.0 g of potassium hydroxide was added in four batches at 10-20 °C. 3. 3. After the potassium hydroxide was added, 1371.1 g of benzyl alcohol was added in three batches. 4. 300.1 g of chloroacetic acid was dissolved in 480.5 g of tetrahydrofuran to prepare a tetrahydrofuran solution of chloroacetic acid. 5. The tetrahydrofuran solution of chloroacetic acid was added dropwise to the above reaction system, and the reaction temperature was maintained at 70-80 °C. 6. 6. React until the chloroacetic acid is completely consumed. 7. Cool the reaction system and add 3.12 kg of purified water. 8. 8. Remove the tetrahydrofuran by pressurized distillation. 9. 9. The aqueous phase was extracted four times with toluene. 10. 10. Adjust the pH of the aqueous phase to 3 with hydrochloric acid at 10-20°C. 11. 11. the aqueous phase was extracted twice with methyl tert-butyl ether. 12. The organic phase was concentrated to give 421.3 g of benzyloxyacetic acid (compound 3) in 88.3% yield and 99.2% GC purity. 13. The product was analyzed by 1H NMR. 13. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 12.28 (br, 1H), 7.34-7.30 (m, 5H), 4.59 (s, 2H), 4.12 (s, 2H).

References

[1] Chemistry - A European Journal, 1999, vol. 5, # 1, p. 121 - 161
[2] Tetrahedron, 2002, vol. 58, # 38, p. 7663 - 7679
[3] European Journal of Organic Chemistry, 2017, vol. 2017, # 3, p. 695 - 703
[4] Patent: US2017/190684, 2017, A1. Location in patent: Paragraph 0065; 0066; 0081
[5] Journal of the American Chemical Society, 2003, vol. 125, # 13, p. 3793 - 3798