Hydrochloric Acid → 2-ethyl-2-(hydroxymethyl)hexanoic Acid

HRID 916284Notes

Reaction equation

C([Li])CCC.[CH2:6]([CH:8]([CH2:12][CH2:13][CH2:14][CH3:15])[C:9]([OH:11])=[O:10])[CH3:7].[H-].[Na+].[CH2:18]=[O:19].[Cl-].[NH4+].Cl>C1COCC1>[CH2:6]([C:8]([CH2:18][OH:19])([CH2:12][CH2:13][CH2:14][CH3:15])[C:9]([OH:11])=[O:10])[CH3:7]

Participants

Conditions

Temperature: 50 °C

Procedure

113 ml (0.305 mol) of n-butyllithium (2.7 M in heptane) are added dropwise at 0° C. to a solution of 46 ml of dissopropylamine (0.327 mol) in 320 ml of THF and the mixture is stirred at 0° C. for 30 min (Solution 1). 40 g (0.277 mol) of 2-ethylhexanoic acid are added dropwise at 25° C. to a suspension of 7 g of NaH 95% (0.277 mol) in 320 ml of THF within approx. 15 min, and the reaction mixture is stirred at 50° C. for 30 min (Solution 2). Solution 1 is added at 0° C. to Solution 2 and subsequently heated to 50° C. for 1.5 h. The clear solution is cooled to −20° C. and admixed with 25 g (0.833 mol) of paraformaldehyde. After 10 min, the mixture is stirred at RT for 18 h. The mixture is admixed with saturated aqueous solution of ammonium chloride and adjusted to pH=1-2 with 6N HCl. The organic phase is removed, the aqueous phase is re-extracted once with MTBE and the combined organic phases are concentrated on a rotary evaporator. The yield of pure product is 70% (GC).

Workup

temperatureThe clear solution is cooled to −20° C.
customThe organic phase is removed
extractionthe aqueous phase is re-extracted once with MTBE
concentrationthe combined organic phases are concentrated on a rotary evaporator

Sources & evidence

ORD record: ord-18b7b3cc5718448f8fa24a4eb4a5f2c2
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268253B2

Reaction notes

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