Trimethylolpropane → Benzoic acid--2-ethyl-2-(hydroxymethyl)propane-1,3-diol (3/1)

HRID 550327Notes

Reaction equation

HRID 550327 reaction equation
[CH2:1]([C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][CH3:5])[OH:2].[C:10](Cl)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(N(CC)CC)C>[C:10]([OH:17])(=[O:2])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:10]([OH:17])(=[O:2])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:10]([OH:17])(=[O:2])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:1]([C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][CH3:5])[OH:2]

Participants

4

Reactant 2

HCID 6510TrimethylolpropaneHCID 7412Benzoyl chloride

Product 1

HCID 23131988Benzoic acid--2-ethyl-2-(hydroxymethyl)propane-1,3-diol (3/1)Yield 85%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixed solution of 45 weight parts of trimethylolpropane and 101 weight parts of triethylamine kept at 100° C. was titrated with 71 weight parts of benzoyl chloride over 30 minutes while stirring, and the resulting solution was further stirred for 30 minutes. The resulting mixture was cooled to room temperature after finishing the reaction and the precipitate was filtered. Then, the filtrate was washed by addition of ethyl acetate pure water; the organic phase was separated and ethyl acetate was removed by evaporation under reduced pressure; whereby 126 weight parts (yield of 85%) of white crystals were obtained. Herein, the molecular weight of this compound was 446.

Workup

  1. customkept at 100° C.
  2. stirringthe resulting solution was further stirred for 30 minutes
  3. customthe reaction
  4. filtrationthe precipitate was filtered
  5. washThen, the filtrate was washed by addition of ethyl acetate pure water
  6. customthe organic phase was separated
  7. customethyl acetate was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-54b3783229c44fd2ad234b65f0f6ac85
Source dataset
uspto-grants-2011_05
Patent number
US07947342B2

Reaction notes

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