Butanoic acid,2-ethyl-3-hydroxyhexyl ester synthesis

8synthesis methods

Product Name:Butanoic acid,2-ethyl-3-hydroxyhexyl ester
CAS Number:18618-89-8
Molecular formula:C12H24O3
Molecular Weight:216.32

123-72-8 Synthesis

123-72-8
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Butanoic acid,2-ethyl-3-hydroxyhexyl ester

18618-89-8
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Butyric acid 1-propyl-2-(hydroxymethyl)butyl ester

18618-91-2
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Yield:-

Reaction Conditions:

with ethyl bromide;magnesium;phenol in N,N,N,N,N,N-hexamethylphosphoric triamide at 45; for 3.5 h;Inert atmosphere;Overall yield = 75 %; Overall yield = 4.5 g;

Steps:

2-ethylhexane-1,3-bis(p-hydroxybenzoate) synthetic scutinin B (2a)2-ethylhexane-1,3-diol (5)

Ethyl bromide (1.2 mL, 16 mmol) was added, dropwise, to a suspension ofmagnesium turnings (0.24 g, 10 mmol) in anhydrous diethyl ether (15 mL)maintained under an atmosphere of nitrogen as to allow a gentle reflux. When all themagnesium was consumed, phenol (0.94 g, 10 mmol) in diethyl ether (5 mL) wasintroduced, dropwise, to the reaction mixture. The solvent was then distilled off andgradually replaced by HMPA (30 mL). Butyraldehyde (9 mL, 0.1 mol) in HMPA (20mL) was then added, dropwise, to the residue and the resulting mixture was allowedto stand at 45 °C for 3.5 h, treated with NH4Cl (20 mL of a saturated aqueoussolution) and extracted with diethyl ether (5 × 20 mL). The combined etherealextracts were washed with KOH (0.1 M; 2 × 50 mL), water (1× 50 mL), dried(Na2SO4), and filtered. The ether was removed under reduced pressure and theresulting oil subjected to kugelrohr distillation (0.05 mmHg, b.p. 79-81 °C; lit.1 0.03mmHg, b.p. 71-72 °C) to afford a mixture of esters 3 and 4 (4.5 g, 70%). This mixture was treated with KOH (9 g) dissolved in 95% aqueous ethanol (75 mL) thenheated at reflux for 3 h, cooled and concentrated under reduced pressure. The residuewas treated with water then extracted with diethyl ether (3 × 50 mL). The combinedethereal extracts were washed with brine (1 × 50 mL), dried (Na2SO4), filtered andconcentrated and kugelrohr distilled (0.05 mmHg, b.p. 67-69 °C; lit.1 0.5 mmHg, b.p.94-96 °C) to afford 2-ethylhexane-1,3-diol (5) (2.9 g, 97%) as a colourless oil. νmax(thin film) 3650-3050, 2985, 2878, 1610, 1485, 1315, 1205, 1015, 1025 cm-1

References:

Chand, Satish;Karuso, Peter [Tetrahedron Letters,2017,vol. 58,# 10,p. 1020 - 1023] Location in patent:supporting information

123-72-8 Synthesis

123-72-8
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109-21-7 Synthesis