Hydrochloric Acid → (E)-2,4-Dichloro-6-phenylmethoxycinnamaldehyde

HRID 1285588Notes

Reaction equation

[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]=1[CH:4]=O.[OH-].[K+].[C:21](OC(=O)C)(=[O:23])[CH3:22].Cl>C(=O)C.O>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]=1/[CH:4]=[CH:22]/[CH:21]=[O:23]

Participants

Conditions

Temperature: 5 °C

Procedure

A stirred suspension of 2,4-dichloro-6-phenylmethoxybenzaldehyde (15.5 g, 55.1 mmole) in acetaldehyde (30 ml) was cooled to 5° C. and treated with 25% methanolic potassium hydroxide (1.4 ml, 6.24 mmole) at such a rate that the internal temperature was maintained at 25°-30° C. The resulting solution was stirred for 30 minutes in the ice bath, treated with acetic anhydride (30 ml) and then heated at 100° C. for 30 minutes. After cooling to 30° C. the solution was treated with water (84 ml) and 12N hydrochloric acid (7 ml). The resulting mixture was refluxed for 30 minutes and then cooled in an ice bath to give a gummy solid which was recrystallized from cyclohexane to give the title compound (5.6 g, 33%), mp 109°-112° C.: pmr (CDCl3) δ 5.10 (2H, s), 7.33 (5H, s), 9.68 (H, d).

Workup

temperaturewas maintained at 25°-30° C
temperatureheated at 100° C. for 30 minutes
temperatureAfter cooling to 30° C. the solution
temperatureThe resulting mixture was refluxed for 30 minutes
temperaturecooled in an ice bath
customto give a gummy solid which
customwas recrystallized from cyclohexane

Sources & evidence

ORD record: ord-c34cc49b8cd24df28ef7c7997dd072e4
Source dataset: uspto-grants-1986_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04567289

Reaction notes

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