7-(tert-Butoxy)-7-oxoheptanoic acid

7-(tert-Butoxy)-7-oxoheptanoic acid Property

Boiling point:

308.7±25.0 °C(Predicted)

Density 

1.038±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

4.74±0.10(Predicted)

Appearance

Colorless to light yellow Liquid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

7-(tert-Butoxy)-7-oxoheptanoic acid Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 7-(tert-butoxy)-7-oxoheptanoic acid from heptanedioic acid and tert-butanol was as follows: heptanedioic acid (1.56 mL, 12.5 mmol), 2-methyl-2-propanol (14.9 mL, 156.3 mmol), EDCI (2.4 g, 12.5 mmol) and DMAP (1.53 g, 12.5 mmol) were dissolved in dichloromethane (15 mL). The reaction mixture was stirred at room temperature for 18 hours. After completion of the reaction, the reaction mixture was diluted with ether (60 mL) and washed sequentially with 0.01 N aqueous HCl and deionized water. The organic phase was dried with anhydrous magnesium sulfate and subsequently concentrated under reduced pressure to remove the solvent. The crude product was purified by column chromatography (eluent ratio 1:1 ethyl acetate:petroleum ether) to afford 7-(tert-butoxy)-7-oxoheptanoic acid (0.52 g, 2.42 mmol, 19% yield) as a colorless oil.1H NMR (400 MHz, DMSO-d6) δ ppm: 12.42 (br s, 1H), 2.18 (q, J = 7.4 Hz, 4H), 1.54-1.43 (m, 4H), 1.40 (s, 9H), 1.32-1.22 (m, 2H).

References

[1] Patent: WO2017/212329, 2017, A1. Location in patent: Page/Page column 29; 81