6-tert-butoxy-6-oxohexanoic acid

6-tert-butoxy-6-oxohexanoic acid Property

Melting point:

10 °C

Boiling point:

116 °C(Press: 1.5 Torr)

Density 

1.054±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

pka

4.69±0.10(Predicted)

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C10H18O4/c1-10(2,3)14-9(13)7-5-4-6-8(11)12/h4-7H2,1-3H3,(H,11,12)

InChIKey

SNOPFBNMUDQLMF-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)CCCCC(O)=O

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H227Combustible liquid

H315Causes skin irritation

H318Causes serious eye damage

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

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.

P310Immediately call a POISON CENTER or doctor/physician.

P321Specific treatment (see … on this label).

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

P362Take off contaminated clothing and wash before reuse.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

6-tert-butoxy-6-oxohexanoic acid Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 6-(tert-butoxy)-6-oxohexanoic acid from the compound (CAS: 52221-08-6) was as follows: tert-butyl adipate (9.9 g, 45.8 mmol) was dissolved in a mixed solvent of ethanol (70 mL) and tetrahydrofuran (70 mL), and the reaction was carried out by slow addition of aqueous sodium hydroxide solution (1 N, 137 mL, 137 mmol) and the reaction was stirred for 2 hours. After completion of the reaction, the mixture was diluted with water and washed with dichloromethane (2 x 70 mL). Subsequently, the mixture was diluted with dichloromethane (100 mL) and acidified with aqueous hydrochloric acid (1 N, 150 mL) to pH ≈ 2. The organic layer was separated and the aqueous phase was further extracted with dichloromethane (2 × 50 mL). All organic layers were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford the title compound 6-(tert-butoxy)-6-oxohexanoic acid (7.82 g, 85% yield). The product was characterized by 1H NMR (C6D6, δ, ppm): 1.48 (9H, s, -OtBu), 1.52 (4H, m, -(CH2)2-), 2.05-2.10 (4H, m, 2*-CH2COO-).

References

[1] Patent: US6414179, 2002, B1
[2] Patent: US2002/65246, 2002, A1
[3] Patent: WO2012/51036, 2012, A1. Location in patent: Page/Page column 77-78