Einecs 211-027-4 → HCID 223474, compound

HRID 260802Notes

Reaction equation

HRID 260802 reaction equation
[Cl-].[NH+]1C=CC=CC=1.[Cl:8][C:9]1[CH:10]=[C:11]([CH:22]=[CH:23][CH:24]=1)[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20]C)[CH:15]=1>>[Cl:8][C:9]1[CH:10]=[C:11]([CH:22]=[CH:23][CH:24]=1)[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=1

Participants

3

Reactant 2

HCID 69401Einecs 211-027-4HCID 534211061-Chloro-3-[2-(3-methoxyphenyl)ethenyl]benzene

Product 1

HCID 223474HCID 223474, compound

Conditions

Temperature
180 °C

Procedure

An excess of triethyl phosphite was added to 3-chlorobenzyl chloride (a), and the mixture was heated with stirring at 130° C. until the generation of ethyl bromide stopped. Diethylchlorobenzyl phosphonate (b) was obtained by the removal of excess triethyl phosphite. Dried dimethylformamide and an excess of sodium methylate were added thereto as a solvent and as a base, respectively, followed by cooling at 0° C. on an ice bath. An equivalent of m-anisaldehyde (c) was added thereto, and the mixture was stirred at room temperature for 1 hour. Then, after stirring at 90° C. for 1 hour, the temperature was lowered to room temperature and stirring was continued overnight. The reaction solution was extracted with ethyl acetate to obtain an ethyl acetate extract. This extract was purified by silica gel chromatography (solvent: hexane/ethyl acetate=9.5/0.5 (V/V)) to obtain 3'-chloro-3-methoxystilbene (d). Subsequently, an excess of pyridinium chloride was added to 3'-chloro-3-methoxystilbene (d), and heated with stirring at 180° C. for 3 hours. The reaction solution was extracted with ethyl acetate, and the resulting ethyl acetate extract was purified by silica gel chromatography (solvent: hexane/ethyl acetate=8.5/1.5 (V/V)) to obtain 3'-chloro-3-hydroxystilbene (compound 4).

Workup

  1. temperatureheated
  2. extractionThe reaction solution was extracted with ethyl acetate
  3. extractionthe resulting ethyl acetate extract
  4. customwas purified by silica gel chromatography (solvent: hexane/ethyl acetate=8.5/1.5 (V/V))

Sources & evidence

ORD record
ord-4a5e3eddf5a5483184f0da89cfb7e4ed
Source dataset
uspto-grants-1996_06
Patent number
US05530030

Reaction notes

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