2,5-dimethoxy-4-ethylbenzaldehyde [CAS 50505-61-8; InChIKey IYHCILMQGOZLJN-UHFFFAOYSA-N; Reaxys, All

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2016-02-22 07h:08m:41s (EST)

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Rx-ID: 22649109 View in Reaxys 1/6 Yield

Conditions & References Reaction Steps: 2 1: Zn-Hg, aq. HCl / ethanol 2: POCl3 With hydrogenchloride, mercury, zinc, trichlorophosphate in ethanol Shulgin; Dyer; Journal of Medicinal Chemistry; vol. 18; nb. 12; (1975); p. 1201 - 1204 View in Reaxys

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Rx-ID: 22680404 View in Reaxys 2/6 Yield

Conditions & References Reaction Steps: 3 1: AlCl3 / CH2Cl2 2: Zn-Hg, aq. HCl / ethanol 3: POCl3 With hydrogenchloride, aluminium trichloride, mercury, zinc, trichlorophosphate in ethanol, dichloromethane Shulgin; Dyer; Journal of Medicinal Chemistry; vol. 18; nb. 12; (1975); p. 1201 - 1204 View in Reaxys

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Rx-ID: 4303423 View in Reaxys 3/6 Yield

Conditions & References With tin(IV) chloride in dichloromethane Nichols; Barfknecht; Rusterholz; Benington; Morin; Journal of medicinal chemistry; vol. 16; nb. 5; (1973); p. 480 - 483 View in Reaxys

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Rx-ID: 1360772 View in Reaxys 4/6 Yield

Conditions & References With trichlorophosphate Aldous,F.A.B. et al.; Journal of Medicinal Chemistry; vol. 17; (1974); p. 1100 - 1111 View in Reaxys Shulgin; Dyer; Journal of Medicinal Chemistry; vol. 18; nb. 12; (1975); p. 1201 - 1204 View in Reaxys

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Conditions & References 17 : Preparation of 2,5-dimethoxy-4-ethyl-phenylacetone EXAMPLE 17 Preparation of 2,5-dimethoxy-4-ethyl-phenylacetone 2,5-dimethoxy-4-ethylbenzaldehyde.

This was prepared by a modification of the method of Rieche, et al. in Org. Syn, 47, 1 (1967).

2,5-dimethoxyethylbenzene(66.4 g, 0.4 mol) was dissolved in 250 ml of dry CH2 Cl2 and cooled to 10° and 208 g (0.8 mol) of anhydrous SnCl4 was added. Cl2 CHOCH3 (45.9 g, 0.4 mol) was then added over 40 minutes, maintaining the temperature at 5° - 10°.

The preparation of 2,5-dimethoxyethylbenzene was reported by Howe, et al. J. Org. Chem, 25 1245 (1960).

Patent; The University of Iowa Research Foundation; US4000197; (1976); (A1) English View in Reaxys

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Rx-ID: 7250669 View in Reaxys 6/6 Yield

Conditions & References entspr. Dimethoxyethylbenzol, Cl2CHOCH3 Patent; Univ. Iowa; US4000197; (1976); ; vol. 86; nb. 139599 View in Reaxys

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