Trimethylolpropane → HCID 178459630, compound

HRID 1691543Notes

Reaction equation

HRID 1691543 reaction equation
[CH2:1]([C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4]C)[OH:2].[CH2:10](C(CO)(C)C)O>CC(C)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2-:10][C:8]([CH3:3])=[O:9].[CH2:1]([C:3]([CH2:8][OH:9])([CH3:4])[CH2:6][OH:7])[OH:2]

Participants

5

Reactant 2

HCID 6510TrimethylolpropaneHCID 31344Neopentyl glycol

Product 1

HCID 178459630HCID 178459630, compoundYield 170.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 180AcetoneSolvent

Procedure

To a stirred solution of trimethylolpropane (TMP) (50.0 g, 373 mmol) in acetone (1000 ml) was added p-toluene sulfonicacid (p-TSA) (1.39 g, 7.46 mmol) and 2,2-dimethylolpropane (58.2 g, 560 mmol). The reaction was stirred over night and quenched with NH4OH/ethanol (50/50 v/v) and the acetone evaporated. The crude product was dissolved in CH2Cl2 (1000 ml), extracted 3 times with water (100 ml), dried with mgSO4, and concentrated to yield a colorless oil (56.5 g, 87%). 1H NMR (CDCl3): δ0.79 (t, CH2CH3, J=7.6 Hz, 3H), 1.30 (q, CH2CH3, J=7.6 Hz, 2H), 1.38 (s, CCH3, 3H), 1.41 (s, CCH3, 3H), 2.70 (t, —OH, J=7.4 Hz, 1H), 3.54 (s, CH2OH, 2H), 3.65 (s, CH2O, 2H), 3.68 (s, CH2O, 2H). 13C NMR (CDCl3): δ7.00 (s, CH2CH3, 1C), 20.17 (s, CH2CH3, 1C), 23.74 (s, CCH3, 1C), 27.30 (s, CCH3, 1C), 36.91 (s, C(CH2)4, 1C), 62.51 (s, CH2OH, 1C), 65.15 (s, CH2O, 2C), 98.16 (s C(CH3)2, 1C).

Workup

  1. customquenched with NH4OH/ethanol (50/50 v/v)
  2. customthe acetone evaporated
  3. dissolutionThe crude product was dissolved in CH2Cl2 (1000 ml)
  4. extractionextracted 3 times with water (100 ml)
  5. customdried with mgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-431b55a04b5a4826ae69b8db0fafd78e
Source dataset
uspto-grants-2012_04
Patent number
US08153729B2

Reaction notes

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