Hexane → (S)-(+)-1-Phenyl-1,2-ethanediol

HRID 1525142Notes

Reaction equation

HRID 1525142 reaction equation
[OH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].CCCCCC>CC(O)C>[C:5]1([C@H:3]([OH:4])[CH2:2][OH:1])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 8058HexaneHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 643312(S)-(+)-1-Phenyl-1,2-ethanediol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

Regarding Example 31, except that the use amount of RuCl[(S)-xylbinap][(S)-daipen] was changed (3.0 mg, 0.0025 mol, 1/1,000 molar fold of 2-hydroxyacetophenone) and 2-propanol (2.5 mL) was used instead of methanol, the same procedure as Example 31 was carried out. As a result of analysis of the reaction solution by using gas chromatography (HP-1), the conversion rate was found to be 99% or more. The optical purity was measured by high performance liquid chromatography (CHIRALPAK AS-H, eluent; hexane:2-propanol=92:8), and it was found to be 90% ee.

Workup

  1. customAs a result of analysis of the reaction solution

Sources & evidence

ORD record
ord-676a51316761443885da18b007c71cfb
Source dataset
uspto-grants-2015_07
Patent number
US09079931B2

Reaction notes

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