Propylene Oxide → HCID 9834706, compound

HRID 889813Notes

Reaction equation

HRID 889813 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[O:5]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:19]1[O:22][CH:20]1[CH3:21]>C(O[Ti](OC(C)C)(OC(C)C)OC(C)C)(C)C>[O:5]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:19][C@@H:20]([OH:22])[CH3:21])=[CH:16][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 132544-PhenoxyphenolHCID 6451240Aluminum(III) Chloride

Product 1

HCID 9834706HCID 9834706, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 178460666HCID 178460666, compoundCatalyst2×

Procedure

In Example 2, 29 mg of tetraisopropoxy titanium was used in place of anhydrous aluminum chloride, and the color of the catalyst solution changed from brown to slightly greenish brown by the addition of tetraisopropoxy titanium. Then 4-phenoxyphenol and propylene oxide were added to the slightly greenish brown catalyst solution to achieve the reaction in the same manner as described in Example 2. Thus (S)-(+)-1-(4-phenoxyphenoxy)-2-propanol was obtained in 84% yield and the optical purity was 95% e.e.

Workup

  1. customthe reaction in the same manner

Sources & evidence

ORD record
ord-9cd6f831e2b444ccb3f5ae1ff9da6ba2
Source dataset
uspto-grants-2006_02
Patent number
US06995110B2

Reaction notes

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