Pentaerythritol → 2,2-Bis(hydroxymethyl)propane-1,3-diyl dibutyrate

HRID 2258548Notes

Reaction equation

HRID 2258548 reaction equation
[C:1]([O:6][CH2:7][C:8]([CH2:23][OH:24])([CH2:16][O:17][C:18](=[O:22])[CH2:19][CH2:20][CH3:21])[CH2:9][O:10][C:11](=[O:15])[CH2:12][CH2:13][CH3:14])(=[O:5])[CH2:2][CH2:3][CH3:4].OCC(CO)(CO)CO.[C:34](Cl)(=[O:38])[CH2:35][CH2:36][CH3:37]>N1C=CC=CC=1>[C:1]([O:6][CH2:7][C:8]([CH2:23][OH:24])([CH2:16][OH:17])[CH2:9][O:10][C:11](=[O:15])[CH2:12][CH2:13][CH3:14])(=[O:5])[CH2:2][CH2:3][CH3:4].[C:11]([O:10][CH2:9][C:8]([CH2:23][O:24][C:34](=[O:38])[CH2:35][CH2:36][CH3:37])([CH2:16][O:17][C:18](=[O:22])[CH2:19][CH2:20][CH3:21])[CH2:7][O:6][C:1](=[O:5])[CH2:2][CH2:3][CH3:4])(=[O:15])[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 8285Pentaerythritol3×HCID 8855Butyryl chloride2×HCID 22922626HCID 22922626, compound

Product 2

HCID 81725Butanoic acid, 2,2-bis[(1-oxobutoxy)methyl]-1,3-propanediyl esterYield 14%HCID 441535362,2-Bis(hydroxymethyl)propane-1,3-diyl dibutyrateYield 26%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In this example, pentaerythritol tributyrate, the tributyl ester of pentaerythritol, was synthesized from pentaerythritol and butyryl chloride as follows. To a solution of pentaerythritol (0.99 g, 7.28mmol) in dry pyridine (50 mL, under argon) at 0° C. was added butyryl chloride (2.3 mL, 22 mmol, 3 equiv) dropwise over one hour. The ice bath was removed after one hour, and the reaction stirred 24 hours at room temperature. Water (7 mL) was added and the bulk of pyridine was removed on the rotary evaporator at 2 Torr. The residue was dissolved in 1N HCL (12 mL) and the pentaerythritol esters extracted with CHCl3 (3×20 mL). The combined organic extracts were dried (MGSO4) and concentrated under vacuum to an oil (2.73 g). Purification by flash column chromatography using silica gel afforded the desired triester pentaerythritol tributyrate (1.34 g; 53%) as well as pentaerythritol dibutyrate (0.51 g; 26%) and pentaerythritol tetrabutyrate (0.42 g; 14%).

Workup

  1. customThe ice bath was removed after one hour
  2. additionWater (7 mL) was added
  3. customthe bulk of pyridine was removed on the rotary evaporator at 2 Torr
  4. dissolutionThe residue was dissolved in 1N HCL (12 mL)
  5. extractionthe pentaerythritol esters extracted with CHCl3 (3×20 mL)
  6. customThe combined organic extracts were dried (MGSO4)
  7. concentrationconcentrated under vacuum to an oil (2.73 g)
  8. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-a10b2e22bc6a4c90985b4b9230e1439c
Source dataset
uspto-grants-1997_08
Patent number
US05661181

Reaction notes

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