Benzoyl chloride → 5-Hydroxypentyl benzoate

HRID 908518Notes

Reaction equation

HRID 908518 reaction equation
[CH:1]([OH:7])(O)[CH2:2][CH2:3][CH2:4][CH3:5].C[Sn](Cl)(Cl)C.[C:13]([O-:16])([O-])=[O:14].[K+].[K+].C(Cl)(=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[C:13]([O:16][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:7])(=[O:14])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 12955Dimethyltin dichlorideHCID 17775877Pentane-1,1-diol

Product 1

HCID 5698735-Hydroxypentyl benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of pentanediol (1 mmol) in THF (5 ml) was added a catalytic amount of dimethyltin dichloride (0.01 mmol), solid K2CO3 (2.0 mmol) and benzoyl chloride (1.2 mmol), at room temperature. After stirring the mixture at room temperature until the diol disappeared (checked by TLC), the mixture was poured onto water and the organic portion was extracted with DCM. After evaporation of the solvent, a residue was obtained and purified by flash chromatography using a mixture of DCM/MeOH as eluent.

Workup

  1. customat room temperature
  2. additionthe mixture was poured onto water
  3. extractionthe organic portion was extracted with DCM
  4. customAfter evaporation of the solvent
  5. customa residue was obtained
  6. custompurified by flash chromatography
  7. additiona mixture of DCM/MeOH as eluent

Sources & evidence

ORD record
ord-12439db56bd543eb8c929760e1c87312
Source dataset
uspto-grants-2011_09
Patent number
US08017620B2

Reaction notes

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