Sorbitol → HCID 14215992, compound

HRID 2098993Notes

Reaction equation

HRID 2098993 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:10][CH2:11][C@@H:12]([C@H:14]([C@@H:16]([C@@H:18]([CH2:20][OH:21])[OH:19])[OH:17])[OH:15])[OH:13]>C(N(CC)CC)C>[C:1]([O:21][CH2:20][C@@H:18]([C@H:16]([C@@H:14]([C@@H:12]([CH2:11][O:10][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[O:13][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[O:15][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[O:17][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[O:19][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5780SorbitolHCID 7412Benzoyl chloride

Product 1

HCID 14215992HCID 14215992, compoundYield 74%

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 30 parts by weight of sorbitol 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 100 parts by weight (at a yield of 74 percent) of white crystals were obtained. The molecular weight of the resulting compound was 809.

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 100 parts by weight (at a yield of 74 percent) of white crystals
  10. customwere obtained

Sources & evidence

ORD record
ord-e8fb132ff853464dbd035ffc142d8d0e
Source dataset
uspto-grants-2009_08
Patent number
US07569259B2

Reaction notes

Loading…