Water → 7-Hydroxyheptyl pivalate

HRID 59633Notes

Reaction equation

HRID 59633 reaction equation
[C:1](Cl)([C:3]([CH3:6])([CH3:5])[CH3:4])=[O:2].N1C=CC=CC=1.[CH2:14]([OH:22])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21].O>C(Cl)(Cl)Cl>[C:1]([O:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][OH:22])(=[O:2])[C:3]([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 123811,7-Heptanediol2×HCID 62493Pivaloyl chloride

Product 1

HCID 874284217-Hydroxyheptyl pivalateYield 68%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Piv-Cl (0.12 ml, 1.0 mmol) and pyridine (0.03 ml, 0.4 mmol) were added to a solution of 1,7-Heptanediol (Compound 26-1, 0.28 ml, 2.0 mmol) in CHCl3 (2 ml) at 0° C., and the mixture was stirred for one day. H2O was added to the reaction solution, the organic layer was then separated, and the aqueous layer was extracted with EtOAc. The combined organic layer was washed with a saturated aqueous NaCl solution, and was dried over Na2SO4. After evaporation of the solvent, the residue was purified by column chromatography on silica gel (Hexane:EtOAc=3:1) to yield 7-hydroxyheptyl pivalate (147 mg, 68%).

Workup

  1. customthe organic layer was then separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organic layer was washed with a saturated aqueous NaCl solution
  4. dry with materialwas dried over Na2SO4
  5. customAfter evaporation of the solvent
  6. customthe residue was purified by column chromatography on silica gel (Hexane:EtOAc=3:1)

Sources & evidence

ORD record
ord-9a37aa06d83240d1880224e7b45fa8da
Source dataset
uspto-grants-2016_09
Patent number
US09440913B2

Reaction notes

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