Diethyl Ether → 3-Hydroxy-2,2-bis(hydroxymethyl)propyl acetate

HRID 2380391Notes

Reaction equation

HRID 2380391 reaction equation
OCC(CO)(CO)CO.[C:10]([O:13][CH2:14][C:15]([CH2:26][O:27]C(=O)C)([CH2:21][O:22]C(=O)C)[CH2:16][O:17]C(=O)C)(=[O:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+].CCOCC>CC(C)=O>[C:10]([O:13][CH2:14][C:15]([CH2:26][OH:27])([CH2:21][OH:22])[CH2:16][OH:17])(=[O:12])[CH3:11]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8285PentaerythritolHCID 11430Potassium CarbonateHCID 69007Pentaerythritol tetraacetate

Product 1

HCID 2954543-Hydroxy-2,2-bis(hydroxymethyl)propyl acetateYield 129.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Pentaerythritol (9.5 grams, 0.07 mol), 7.0 grams (0.02 mol) of pentaerythritol tetraacetate and 500 mg of potassium carbonate were heated for 12 hours at 180° C. A light brown solution resulted which was boiled for 15 minutes in 50 ml of acetone and the resulting precipitate was filtered off. The filtrate was concentrated and passed through a plug of silica gel using acetone as a solvent. The mixture was purified by flash chromatography (1:1, CHCl3 :acetone) to yield a product of Rf =0.1. Addition of 25 ml of ether caused the product to solidify, yielding 4.6 grams of pentaerythritol monoacetate as a white solid.

Workup

  1. customA light brown solution resulted which
  2. filtrationthe resulting precipitate was filtered off
  3. concentrationThe filtrate was concentrated
  4. customThe mixture was purified by flash chromatography (1:1, CHCl3 :acetone)
  5. customto yield a product of Rf =0.1

Sources & evidence

ORD record
ord-d404db3041b5490eac90150b718d8c6e
Source dataset
uspto-grants-1994_11
Patent number
US05367061

Reaction notes

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