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

HRID 2098992Notes

Reaction equation

HRID 2098992 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)

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 to 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 temperature was lowered to room temperature and the resulting precipitates were collected by filtration. Thereafter, washing was performed by adding ethyl acetate-pure water. Subsequently, the organic phase was collected and ethyl acetate was distilled out under vacuum, whereby 126 parts by weight (at a yield of 85 percents) of white crystals were obtained. 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. customwas lowered to room temperature
  4. customthe resulting precipitates
  5. filtrationwere collected by filtration
  6. washThereafter, washing
  7. additionby adding ethyl acetate-pure water
  8. customSubsequently, the organic phase was collected
  9. distillationethyl acetate was distilled out under vacuum, whereby 126 parts by weight (at a yield of 85 percents) of white crystals
  10. customwere obtained

Sources & evidence

ORD record
ord-d5060ff6341449469bde122d2eb6ba0a
Source dataset
uspto-grants-2009_08
Patent number
US07569259B2

Reaction notes

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