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Triphenylphosphine → [(E)-cinnamyl]-triphenyl-phosphonium chloride

HRID 274192
Notes
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Reaction equation

HRID 274192 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]([Cl:29])[CH:21]=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1(C)C(C)=CC=CC=1>[Cl-:29].[CH2:20]([P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH:21]=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 94242Benzene, (3-chloro-1-propenyl)-

Product 1

HCID 73729[(E)-cinnamyl]-triphenyl-phosphonium chloride

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

88.2 parts of triphenylphosphine was dissolved in 240 parts of xylene and 51.3 parts of cinnamyl chloride was added thereto. The mixture was heated at 130° C. for 4 hr. After the mixture was cooled to 30° C., the resulting colorless crystals were collected by filtration and washed with toluene to obtain 117.4 parts of cinnamyltriphenylphosphonium chloride (compound No. 15).

Workup

  1. additionwas added
  2. temperatureAfter the mixture was cooled to 30° C.
  3. filtrationthe resulting colorless crystals were collected by filtration
  4. washwashed with toluene

Sources & evidence

ORD record
ord-fa939c3d200942e0a4f0c4e26a59ee5a
Source dataset
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05389486

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes