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Thionyl Chloride → HCID 53773575, compound

HRID 1612590
Notes
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Reaction equation

HRID 1612590 reaction equation
[CH2:1]([O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH2:10].S(Cl)([Cl:23])=O>C1(C)C=CC=CC=1>[CH:1]([O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([Cl:23])=[O:17])=[CH:14][CH:13]=1)=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 148765254-(9-Decen-1-yloxy)benzoic acid

Product 1

HCID 53773575HCID 53773575, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To 2.8 g of p-(9-decenyloxy)benzoic acid prepared in the same manner as in 9.(2) in Example 9 added was toluene, and the resulting mixture was cooled in an ice bath. 5.0 g of thionyl chloride was then added dropwise to the toluene solution. Reaction was then carried out for 7 hours at 80° C. After conclusion of the reaction, the reaction solution was concentrated under reduced pressure, to obtain crude p-decenyloxybenzoyl chloride. 1.6 g of the hydroxy compound obtained in 17.(1) and 3.3 g of pyridine were dissolved in toluene, and the resulting toluene solution was cooled in an ice bath. A toluene solution containing the above crude p-decenyloxybenzoyl chloride was added dropwise into the toluene solution. Subsequently, reaction was carried out for 5 hours at 50° C. After conclusion of the reaction, the reaction solution was washed with water and dried over magnesium sulfate, and the solvent was distilled out under reduced pressure. The residue was purified by column chromatography, to obtain 2.0 g of the objective alkene compound. (Yield: 69%)

Workup

  1. additionadded
  2. temperaturethe resulting mixture was cooled in an ice bath
  3. customReaction
  4. customAfter conclusion of the reaction
  5. concentrationthe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e0135dd47e8d4a1599b38862a642e93c
Source dataset
uspto-grants-1993_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05190686

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes