Pentaerythritol → HCID 22922627, compound

HRID 2258550Notes

Reaction equation

HRID 2258550 reaction equation
OC[C:3]([CH2:8][OH:9])([CH2:6]O)CO.[C:10]([O:15][CH2:16][C:17]([CH2:27][OH:28])([CH2:25][OH:26])[CH2:18][O:19][C:20](=[O:24])[CH2:21][CH2:22][CH3:23])(=[O:14])[CH2:11][CH2:12][CH3:13].[C:29](Cl)(=[O:32])[CH2:30][CH3:31]>N1C=CC=CC=1>[C:29]([O:26][CH2:25][C:17]([CH2:27][O:28][C:8](=[O:9])[CH2:3][CH3:6])([CH2:18][O:19][C:20](=[O:24])[CH2:21][CH2:22][CH3:23])[CH2:16][O:15][C:10](=[O:14])[CH2:11][CH2:12][CH3:13])(=[O:32])[CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 8285PentaerythritolHCID 62324Propionyl chlorideHCID 441535362,2-Bis(hydroxymethyl)propane-1,3-diyl dibutyrate2×

Product 1

HCID 22922627HCID 22922627, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In this example, pentaerythritol dibutyratedipropionate was prepared from pentaerythritol dibutyrate as follows. To a solution of pentaerythritol dibutyrate (0.5 g; 1.81 mmol) in dry pyridine (10 mL, under argon) at 0° C. was added propionyl chloride (0.6 mL) dropwise over one hour. The ice bath was removed after one hour, and the reaction stirred 24 hours at room temperature. Water (5 mL) was added and the bulk of pyridine was removed on the rotary evaporator at 2 Torr. The residue was dissolved in 1N HCL (5 mL) and the desired product extracted with CHCl3 (2×20 mL). The combined organic extracts were dried (MgSO4) and concentrated under vacuum. Purification of the crude product by flash column chromatography using silica gel afforded pentaerythritol dibutyrate dipropionate (0.6 g).

Workup

  1. customThe ice bath was removed after one hour
  2. additionWater (5 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 (5 mL)
  5. extractionthe desired product extracted with CHCl3 (2×20 mL)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. concentrationconcentrated under vacuum
  8. customPurification of the crude product by flash column chromatography

Sources & evidence

ORD record
ord-489c760d37fb4af0a79cb7cedf0f9f40
Source dataset
uspto-grants-1997_08
Patent number
US05661181

Reaction notes

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