2,3-DIHYDROBENZOFURAN-7-CARBOXYLIC ACID Chemical Properties

Melting point:

169-171

Boiling point:

330.6±31.0 °C(Predicted)

Density 

1.344±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

powder to crystal

pka

4.16±0.20(Predicted)

color 

White to Orange to Green

InChI

InChI=1S/C9H8O3/c10-9(11)7-3-1-2-6-4-5-12-8(6)7/h1-3H,4-5H2,(H,10,11)

InChIKey

UHXBMSNEECJPSX-UHFFFAOYSA-N

SMILES

O1C2=C(C(O)=O)C=CC=C2CC1

CAS DataBase Reference

35700-40-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-51

HazardClass 

IRRITANT

HS Code 

2932990090

2,3-DIHYDROBENZOFURAN-7-CARBOXYLIC ACID Usage And Synthesis

Synthesis

1. Synthesis of 2,3-dihydrobenzo[b]furan-7-carboxylic acid (15a): N,N,N',N'-tetramethylethylenediamine (TMEDA) (24.3 g, 0.21 mol) was added dropwise to a solution of n-BuLi (1.7 M, 123 mL, 0.21 mol) in 400 mL of hexanes under argon protection followed by the addition of a solution of 2,3-dihydrobenzo[b ] furan (14) (12.56 g, 0.11 mol) solution in hexane (40 mL). The reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was slowly poured into dry ice pre-washed with anhydrous ether, followed by stirring at room temperature overnight. After completion of the reaction, the organic and aqueous layers were separated by diluting the mixture with 300 mL of water. The aqueous layer was acidified to pH 1 with concentrated hydrochloric acid and precipitated as a white solid upon cooling. The precipitate was collected by filtration and recrystallized with dichloromethane (CH2Cl2) to give the target product 15a (9.43 g, 54.7% yield) as a white solid with a melting point of 167-169.5 °C.

References

[1] Patent: US4888353, 1989, A
[2] Patent: EP234872, 1991, B1
[3] Patent: US5122361, 1992, A

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