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

HRID 354565Notes

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 12 N 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) δ5.10 (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-59a17bf264f545af9b54af5e1b0f4023
Source dataset: uspto-grants-1983_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04375475

Reaction notes

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