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Diethyl Ether → trans-Stilbene

HRID 429607
Notes
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Reaction equation

HRID 429607 reaction equation
[CH3:1]CCCCCCCCC.CC[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(OCC)C>>[C:21]1(/[CH:20]=[CH:19]/[C:18]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1.[C:21]1(/[CH:20]=[CH:19]\[C:18]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1.[C:21]1([C:20]([C:19]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH2:1])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 11006HexadecaneHCID 15600Decane

Product 3

HCID 107401,1-DiphenylethyleneYield 13.2%HCID 638088trans-StilbeneYield 86.5%HCID 5356785cis-StilbeneYield 0.3%

Procedure

After the reaction, the GC standards n-decane and n-hexadecane are added, and 3 ml of diethyl ether is added to the mixture. After filtering off the solids, the filtrate is examined by gas chromatography: With 78.5% conversion of Cl-benzene, an 80% yield of Heck products (86.5% trans-stilbene, 0.3% cis-stilbene, and 13.2% 1,1-diphenylethene) is obtained.

Workup

  1. customAfter the reaction
  2. filtrationAfter filtering off the solids

Sources & evidence

ORD record
ord-f3a777079160482a87d4855a87394aa2
Source dataset
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06316675B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes