Monobenzone → Methyl 2-[p-(benzyloxy)phenoxy]propionate

HRID 853154Notes

Reaction equation

HRID 853154 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:17]([CH3:22])[C:18]([O:20][CH3:21])=[O:19].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH3:21][O:20][C:18](=[O:19])[CH:17]([O:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)[CH3:22]

Participants

5

Reactant 3

HCID 7638MonobenzoneHCID 10796Cesium carbonateHCID 95576Methyl 2-bromopropionate

Product 1

HCID 13093988Methyl 2-[p-(benzyloxy)phenoxy]propionate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In analogy to the procedure described in Example 1b), the alkylation of 4-benzyloxy-phenol [Example 2a)] with methyl (RS)-2-bromopropionate in acetone using cesium carbonate as the base yielded the (RS)-2-(4-Benzyloxy-phenoxy)-propionic acid methyl ester as light yellow oil; MS: m/e=304 (M+NH4)+.

Sources & evidence

ORD record
ord-fc1bbd4eea9c4f278f67d31592e7bb8f
Source dataset
uspto-grants-2007_08
Patent number
US07253318B2

Reaction notes

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