4-METHOXYCARBONYLMETHYL-BENZOIC ACID METHYL ESTER Chemical Properties

Melting point:

20 °C

Boiling point:

122°C/0.6mmHg(lit.)

Density 

1.155

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

color 

White to Pale Yellow

InChI

InChI=1S/C11H12O4/c1-14-10(12)7-8-3-5-9(6-4-8)11(13)15-2/h3-6H,7H2,1-2H3

InChIKey

QAQYBHOZQQRJBA-UHFFFAOYSA-N

SMILES

C1(CC(OC)=O)=CC=C(C(OC)=O)C=C1

Safety Information

HS Code 

2917.39.7000

4-METHOXYCARBONYLMETHYL-BENZOIC ACID METHYL ESTER Usage And Synthesis

Uses

4-Methoxycarbonylmethyl-benzoic acid methyl ester is an intermediate for the preparation of 10-Propargyl-10-deazaaminopterin with anti tumor activity.

Synthesis

To the reaction flask was added 4-(carboxymethyl)benzoic acid (5 g, 27.78 mmol), 75 ml of methanol was added to dissolve the raw material and continued with 0.5 ml of N,N-dimethylformamide and thionyl chloride (6 ml, 83.33 mmol). The reaction was carried out at 50°C for 4 hours. After completion of the reaction, most of the thionyl chloride and methanol were removed by rotary evaporation. The residue was dissolved in 200 ml of ethyl acetate and washed sequentially with saturated sodium carbonate solution (50 ml x 3) and saturated brine (50 ml x 3). The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated by rotary evaporation to give 5.5 g of a colorless transparent liquid product, methyl 4-formate phenylacetate, in 95.2% yield.

References

[1] Patent: CN105541777, 2016, A. Location in patent: Paragraph 0015; 0059; 0060; 0061
[2] Journal of Medicinal Chemistry, 1997, vol. 40, # 3, p. 377 - 384
[3] Patent: WO2015/100363, 2015, A1. Location in patent: Page/Page column 52; 53
[4] Patent: CN103739604, 2016, B. Location in patent: Paragraph 0037-0038
[5] Journal of the Indian Chemical Society, 1987, vol. 64, # 1, p. 34 - 37

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