Epichlorohydrin → 1-(4-Benzyloxy-3,5-dimethylphenoxy)-2,3-epoxypropane

HRID 277640Notes

Reaction equation

HRID 277640 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([OH:16])=[CH:11][C:10]=1[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:19][CH:20]1[CH2:22][O:21]1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH2:1]([O:8][C:9]1[C:10]([CH3:17])=[CH:11][C:12]([O:16][CH2:19][CH:20]2[O:21][CH2:22]2)=[CH:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 226253934-(Benzyloxy)-3,5-dimethylphenol

Product 1

HCID 226254101-(4-Benzyloxy-3,5-dimethylphenoxy)-2,3-epoxypropane

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Using 4.22 g of the compound of Example 15, 2.7 ml of chloromethyloxirane, 2.42 g of anhydrous potassium carbonate and 100 ml of methyl ethyl ketone, reaction and workup carried out as in Example 1-A gave about 4.80 g of 1-(4-benzyloxy-3,5-dimethylphenoxy)-2,3-epoxypropane as yellow oil. Using the epoxy compound thus obtained, 4.04 g of 1-(2-methoxyphenyl)piperazine and 100 ml of dioxane, reaction and workup carried out as in Example 1-A followed by purification by column chromatography (silica gel, eluted with ethyl acetate:hexane=1:1) gave 5.96 g of white crystals, m.p. 93-94° C.

Sources & evidence

ORD record
ord-a7faaccca8864e83be11141c32b52dac
Source dataset
uspto-grants-2002_03
Patent number
US06358515B2

Reaction notes

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