Propylene Oxide → HCID 9834706, compound

HRID 889815Notes

Reaction equation

HRID 889815 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 77%

Reagents, catalysts & solvents 1

HCID 178460666HCID 178460666, compoundCatalyst2×

Procedure

In Example 2, the amount of (R,R)-(−)-N,N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamino cobalt (III) 4-phenoxyphenolate used was changed to 41 mg, and 15 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 77% yield and the optical purity was 94% e.e.

Workup

  1. customthe reaction in the same manner

Sources & evidence

ORD record
ord-8b147c7f0fa14e96a7b236f2ae998ad1
Source dataset
uspto-grants-2006_02
Patent number
US06995110B2

Reaction notes

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