Sodium Hydroxide → sodium (Z)-3-(4-chlorophenyl)-3-(4-methanesulfonylphenyl)-2-(2-hydroxyethyl)prop-2-enoate

HRID 357267Notes

Reaction equation

HRID 357267 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[C:9](/[CH2:15][CH2:16][OH:17])\[C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+:29]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[C:18]2[CH:19]=[CH:20][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][CH:23]=2)=[C:9](/[CH2:15][CH2:16][OH:17])\[C:10]([O-:12])=[O:11])=[CH:4][CH:3]=1.[Na+:29]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11112334ethyl (Z)-3-(4-chlorophenyl)-3-(4-methanesulfonylphenyl)-2-(2-hydroxyethyl)-2-propenoate

Product 1

HCID 23676214sodium (Z)-3-(4-chlorophenyl)-3-(4-methanesulfonylphenyl)-2-(2-hydroxyethyl)prop-2-enoateYield 101.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5 g (0.0122 mole) of ethyl (Z)-3-(4-chlorophenyl)-3-(4-methanesulfonylphenyl)-2-(2-hydroxyethyl)prop-2-enoate, prepared in example 4, in 10 ml of ethanol are added 11 ml (0.011 mole) of 1M sodium hydroxide. The mixture is heated for 2 hours under reflux, then evaporated to dryness in vacuo. The crystals obtained are washed with ethyl acetate and with ethyl ether and then dried to provide 4.5 g of sodium (Z)-3-(4-chlorophenyl)-3-(4-methanesulfonylphenyl)-2-(2-hydroxyethyl)prop-2-enoate as crystals with a melting point of 257°-259° C.

Workup

  1. temperatureThe mixture is heated for 2 hours
  2. temperatureunder reflux
  3. customevaporated to dryness in vacuo
  4. customThe crystals obtained
  5. washare washed with ethyl acetate and with ethyl ether
  6. customdried

Sources & evidence

ORD record
ord-bfc3b98199864f76bd51860cce168947
Source dataset
uspto-grants-1998_11
Patent number
US05840753

Reaction notes

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