Propylene Oxide → HCID 9834706, compound

HRID 889808Notes

Reaction equation

HRID 889808 reaction equation
[Cl-].C([Al+]CC)C.CCCCCC.[Cl-].[Al+3].[Cl-].[Cl-].[O:17]([C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH2:31]1[O:34][CH:32]1[CH3:33]>>[O:17]([C:24]1[CH:25]=[CH:26][C:27]([O:30][CH2:31][C@@H:32]([OH:34])[CH3:33])=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 6378Propylene OxideHCID 132544-PhenoxyphenolHCID 6451240Aluminum(III) ChlorideHCID 22247693HCID 22247693, compound2×

Product 1

HCID 9834706HCID 9834706, compoundYield 72%

Procedure

In Example 2, 0.1 mL of a diethyl aluminum chloride/hexane solution was used in place of anhydrous aluminum chloride, and the color of the catalyst solution changed from brown to dark green by the addition of a diethyl aluminum chloride/hexane solution. Then 4-phenoxyphenol and propylene oxide were added to the dark green 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 72% yield and the optical purity was 87% e.e.

Workup

  1. customthe reaction in the same manner

Sources & evidence

ORD record
ord-42d62dd9d3ca406894f334d550abc088
Source dataset
uspto-grants-2006_02
Patent number
US06995110B2

Reaction notes

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