반응 #502079

반응 방정식

Ethyl acetate

Aluminium chloride

lithium aluminium hydride

2-methyl-2-(4-methylpentyl)-1,3-dioxolane

lithium aluminium hydride

→

desired product

2-[(1,5-dimethylhexyl)oxy]ethanol

용매

Tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   기타fitted with condenser
2. 2
   온도The flask was cooled to <10° C.
3. 3
   온도whilst maintaining a temperature of <10° C
4. 4
   workup.STIRRINGas stirred for 2 hours at <10° C
5. 5
   온도cooling
6. 6
   기타The crude reaction mixture
7. 7
   추출was extracted into methyltert-butyl ether (2×300 mL)
8. 8
   세척the organic phase washed with water (200 mL)
9. 9
   건조The organic phase was dried over magnesium sulphate
10. 10
    여과filtered
11. 11
    기타the solvent removed by evaporation

실험 절차

Tetrahydrofuran (600 mL) was charged to 2 L flask fitted with condenser, nitrogen, thermocouple and mechanical stirrer. The flask was cooled to <10° C. and the flask was inerted with dry nitrogen fed a slow rate. Aluminium chloride (112 g, 840 mmol) was slowly added to the reaction flask whilst maintaining a temperature of <10° C. Then lithium aluminium hydride powder (15.9 g, 420 mmol) was added slowly over 30 minutes. The reaction mixture was stirred for a further 30 minutes at <10° C. To the reaction flask was added slowly a solution of 2-methyl-2-(4-methylpentyl)-1,3-dioxolane (72 g, 420 mmol) in tetrahydrofuran (50 mL) over 30 minutes. The reaction mixtures as stirred for 2 hours at <10° C. Ethyl acetate (200 g) was then added slowly to the reaction mixture to neutralise the excess lithium aluminium hydride—cooling was necessary to counteract the large exotherm. The crude reaction mixture was extracted into methyltert-butyl ether (2×300 mL) and the organic phase washed with water (200 mL). The organic phase was dried over magnesium sulphate, filtered and the solvent removed by evaporation to yield the desired product suitable for the next synthetic step as a colourless oil (100% pure by GC rpa, 70 g, 400 mmol, 96% chemical yield). A small sample was Kugelrohr distilled to give material suitable for olfactive analysis.

출처