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

HRID 1399418Notes

Reaction equation

HRID 1399418 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([C:12]([CH2:17][OH:18])([CH2:15][OH:16])[CH2:13][CH3:14])[OH:11]>C(N(CC)CC)C>[C:1]([OH:8])(=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:1]([OH:8])(=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:1]([OH:8])(=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([C:12]([CH2:17][OH:18])([CH2:15][OH:16])[CH2:13][CH3:14])[OH:11]

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

Conditions

Temperature
100 °C

Procedure

While stirring, 71 parts by weight of benzoyl chloride were dripped over 30 minutes into a mixed solution of 45 parts by weight of trimethylolpropane and 101 parts by weight of triethylamine maintained at 100° C., and the resulting mixture was stirred for an additional 30 minutes. After completion of the reaction, the resulting mixture was cooled to room temperature. After collecting precipitates via filtration, washing was carried out via the addition of ethyl acetate and pure water, and the organic phase was collected via separation, followed by removal of ethyl acetate via distillation under reduced pressure, whereby 126 parts by weight (at an 85% yield) of white TMPTB crystals were prepared. The molecular weight of the resulting compound was 446.

Workup

  1. stirringthe resulting mixture was stirred for an additional 30 minutes
  2. customAfter completion of the reaction
  3. temperaturethe resulting mixture was cooled to room temperature
  4. customAfter collecting
  5. customprecipitates via filtration
  6. washwashing
  7. additionwas carried out via the addition of ethyl acetate and pure water
  8. customthe organic phase was collected via separation
  9. customfollowed by removal of ethyl acetate via distillation under reduced pressure, whereby 126 parts by weight (at an 85% yield) of white TMPTB crystals
  10. customwere prepared

Sources & evidence

ORD record
ord-422746ef4ea548f6b197dc5c198973f1
Source dataset
uspto-grants-2014_12
Patent number
US08906279B2

Reaction notes

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