8-(tert-Butoxy)-8-oxooctanoic acid

8-(tert-Butoxy)-8-oxooctanoic acid Property

Boiling point:

324.8±25.0 °C(Predicted)

Density 

1.024±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

4.76±0.10(Predicted)

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C12H22O4/c1-12(2,3)16-11(15)9-7-5-4-6-8-10(13)14/h4-9H2,1-3H3,(H,13,14)

InChIKey

BONUHUQZCZQQEN-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)CCCCCCC(O)=O

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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).

P330Rinse mouth.

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

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

8-(tert-Butoxy)-8-oxooctanoic acid Chemical Properties,Usage,Production

Uses

8-(tert-butoxy)-8-oxooctanoic acid can be used as an intermediate in the production of complex organic molecules.

Synthesis

The general procedure for the synthesis of 8-(tert-butoxy)-8-oxooctanoic acid from octanedioic acid and tert-butanol was as follows: octanedioic acid (1.00 g, 5.75 mmol), 2-methyl-2-propanol (6.9 mL, 71.8 mmol), EDCI (1.1 g, 5.74 mmol) and DMAP (0.7 g, 5.74 mmol) were dissolved in dichloromethane ( 6.8 mL). The reaction mixture was stirred at room temperature for 5 hours. After completion of the reaction, the reaction mixture was diluted with ether (60 mL) and washed sequentially with 0.01 N HCl (50 mL) and water (50 mL). 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 fast column chromatography with the eluent being 1:1 ethyl acetate:petroleum ether to afford 8-(tert-butoxy)-8-oxooctanoic acid (0.41 g, 1.77 mmol, 31% yield) as a colorless oil.1H NMR (400 MHz, DMSO-d6) δ ppm: 11.94 (broad single peak, 1H), 2.18 (double peak, J = 14.6, 7.3 Hz, 4H), 1.54-1.42 (multiple peaks, 4H), 1.40 (single peak, 9H), 1.34-1.20 (multiple peaks, 4H).

References

[1] Patent: WO2017/212329, 2017, A1. Location in patent: Page/Page column 30; 83; 84
[2] Chemistry and Physics of Lipids, 2002, vol. 119, # 1-2, p. 51 - 68
[3] Chemical Communications, 1999, # 9, p. 823 - 824