p-Toluenesulfonic acid monohydrate → Ethyl 3-[4-(2-hydroxyethoxy)phenyl]-2-phenoxypropionate

HRID 1859958Notes

Reaction equation

HRID 1859958 reaction equation
[O:1]([CH:8]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][O:24]C2CCCCO2)=[CH:17][CH:16]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[OH:24][CH2:23][CH2:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 18625831Ethyl 2-phenoxy-3-[4-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl]propionate

Product 1

HCID 18625939Ethyl 3-[4-(2-hydroxyethoxy)phenyl]-2-phenoxypropionateYield 90.8%

Procedure

In a similar manner to that described in Reference example 3(f), a reaction was carried out using ethyl 2-phenoxy-3-[4-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl]propionate (4.53 g), which is the product of Reference example 4(d), and p-toluenesulfonic acid monohydrate (2.70 g) and the reaction mixture was treated to afford the desired compound (3.28 g) as a syrup.

Workup

  1. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-2abdc3aedf434663b17af9eab9b48738
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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