ChemicalBook CAS DataBase List tert-Butyl 6-Hydroxyhexanoate

tert-Butyl 6-Hydroxyhexanoate synthesis

10synthesis methods

Product Name:tert-Butyl 6-Hydroxyhexanoate
CAS Number:73839-20-0
Molecular formula:C10H20O3
Molecular Weight:188.26

502-44-3 Synthesis

502-44-3
343 suppliers
$5.00/25g

75-65-0 Synthesis

75-65-0
750 suppliers
$10.00/10ml

73839-20-0
56 suppliers
$140.00/1g

Yield: 80%

Reaction Conditions:

with potassium tert-butylate in dichloromethane for 3 h;Reflux;Inert atmosphere;

Steps:

3.1 Preparation of 6-Hydroxy-hexanoic acid tert-butyl ester (15)
To a 250 mL round bottom flask equipped with a magnetic stirrer, thermocouple, condenser and nitrogen inlet was charged 6-hexanolactone 14 (3.7 g; 32 mmol) and i-BuOH (100 mL) in DCM followed by i-BuOK (3.9 g; 35 mmol; 1.1 equiv.). This solution was stirred and heated to reflux for 3 hours. The solution was diluted with toluene, washed with water and brine, dried over Na₂S0₄, filtered and concentrated to afford 4.8 g (80% yield) as a clear yellow oil. 1H-NMR (500 MHz, CDC1₃): δ 3.65 - 3.62 (m, 2H), 2.32 - 2.29 (m, 1H), 2.23 - 2.20 (m, 2H), 1.66 - 1.55 (m, 4H), 1.43 (s, 9H), 1.41 - 1.35 (m, 2H).

References:

REGENERON PHARMACEUTICALS, INC.;NITTOLI, Thomas;KUNZ, Arthur WO2015/187596, 2015, A2 Location in patent:Paragraph 00244