Chloride → HCID 18950146, compound

HRID 2379655Notes

Reaction equation

HRID 2379655 reaction equation
S(Cl)(Cl)=O.[C:5]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)(=[O:7])[CH3:6].[C:18]1(C)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Cl-]>ClCCl.N1C=CC=CC=1>[C:5]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([O:15][CH:23]([CH3:22])[CH2:18][CH2:19][CH2:20][CH3:21])=[O:14])=[CH:11][CH:10]=1)(=[O:7])[CH3:6]

Participants

7

Reactant 4

HCID 312ChlorideHCID 1140TolueneHCID 16865Benzoic acid, 4-(acetyloxy)-HCID 24386Thionyl Chloride

Product 1

HCID 18950146HCID 18950146, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (25 ml) was added to 10 mmols of p-acetoxybenzoic acid, and the mixture was refluxed for 5 hours. Excess thionyl chloride was then completely removed. Thirty milliliters of toluene were added to the obtained chloride, and 7.1 mmols of R-(-)-2-hexanol and 3 ml of pyridine were added dropwise, followed by conducting the reaction overnight at room temperature. After the reaction, 50 ml of dichloromethane was added, and the organic layer was washed with a hydrochloric acid aqueous solution, a sodium hydroxide aqueous solution and water in this sequence. Subsequently, the organic layer was dried over anhydrous sodium sulfate, and the solvent was removed. The obtained composition was purified by silica gel column chromatography to obtain 1-methylpentyl p-acetoxybenzoate in a yield of 87%.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. customExcess thionyl chloride was then completely removed
  3. additionwere added dropwise
  4. customthe reaction overnight at room temperature
  5. additionwas added
  6. washthe organic layer was washed with a hydrochloric acid aqueous solution
  7. dry with materialSubsequently, the organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was removed
  9. customThe obtained composition was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-061859ff54a14aa5acc2bd895f9a43a9
Source dataset
uspto-grants-1994_11
Patent number
US05364560

Reaction notes

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