Benzene → (S,S)-(-)-HYDROBENZOIN

HRID 1721507Notes

Reaction equation

HRID 1721507 reaction equation
[C@@H:1]1(N)[CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]1N.[OH2:9].[CH:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl.[CH2:17]([OH:19])[CH3:18]>>[C:1]1([C@H:18]([OH:9])[C@H:17]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[OH:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 5

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 438061,2-Diaminocyclohexane, trans-

Product 1

HCID 853020(S,S)-(-)-HYDROBENZOINYield 61%

Procedure

0.874 g (7.65 mmol) of (1R,2R)-(-)-1,2-cyclohexanediamine of α!D20 =-36°-7° (c 4.14, H2O) and 1.63 g (7.61 mmol) of dl-threo-1,2-diphenyl-1,2-ethanediol were added to 7 ml of benzene and then heated/dissolved therein, and the solution was cooled to room temperature. Afterward, the precipitated crystals were collected by filtration and then recrystallized from 5 ml of benzene to obtain 0.765 g (2.33 mmol) of (1R,2R)-(-)-1,2-cyclohexanediamine·(1S,2S)-(-)-1,2-diphenyl-1,2-ethanediol complex. 1 ml of ethanol and 10 ml of 1M hydrochloric acid were added to the above-mentioned crystals under ice cooling, followed by stirring for 30 minutes. The solution was extracted with methylene chloride, washed with water, dried over anhydrous sodium sulfate, and then concentrated to obtain 0.499 g (2.33 mmol) of (1S,2S)-(-)-1,2-diphenyl-1,2-ethanediol.

Workup

  1. dissolutionheated/dissolved
  2. filtrationAfterward, the precipitated crystals were collected by filtration
  3. customrecrystallized from 5 ml of benzene
  4. customto obtain 0.765 g (2.33 mmol) of (1R,2R)-(-)-1,2-cyclohexanediamine·(1S,2S)-(-)-1,2-diphenyl-1,2-ethanediol complex
  5. extractionThe solution was extracted with methylene chloride
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c1c8528fb681427dbf5f7ff0f0606ea7
Source dataset
uspto-grants-1996_04
Patent number
US05510520

Reaction notes

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