2-Mercaptoethanol → HCID 13885751, compound

HRID 1164930Notes

Reaction equation

HRID 1164930 reaction equation
[SH:1][CH2:2][CH2:3][OH:4].C[O-].[Na+].[C:8]([C:11]1[CH:21]=[CH:20][C:14]([O:15][CH2:16][CH2:17][CH2:18]Br)=[C:13]([CH2:22][CH2:23][CH3:24])[C:12]=1[OH:25])(=[O:10])[CH3:9]>>[C:8]([C:11]1[CH:21]=[CH:20][C:14]([O:15][CH2:16][CH2:17][CH2:18][S:1][CH2:2][CH2:3][OH:4])=[C:13]([CH2:22][CH2:23][CH3:24])[C:12]=1[OH:25])(=[O:10])[CH3:9]

Participants

4

Reactant 3

HCID 15672-MercaptoethanolHCID 27752211-[4-(3-bromopropoxy)-2-hydroxy-3-propylphenyl]ethanoneHCID 10942334Sodium Methoxide

Product 1

HCID 13885751HCID 13885751, compound

Procedure

4.68 g. (60 mMole) 2-mercaptoethanol are stirred for 10 minutes at ambient temperature with 60 ml. 1M sodium methylate solution. Subsequently, 9.39 g. 3-(4-acetyl-3-hydroxy-2-propylphenoxy)-propyl bromide are added thereto and the reaction mixture is boiled under reflux for 5 hours. The reaction mixture is thereafter evaporated and the residue mixed with water and ethyl acetate. The ethyl acetate phase is successively shaken with 2M aqueous sodium hydroxide solution and with 2M hydrochloric acid and then dried and evaporated. After recrystallising the residue from diethyl ether/ligroin, there are obtained 6.4 g. (68% of theory) of the title compound; m.p. 72°-74° C.

Workup

  1. temperatureunder reflux for 5 hours
  2. customThe reaction mixture is thereafter evaporated
  3. additionthe residue mixed with water and ethyl acetate
  4. customdried
  5. customevaporated
  6. customAfter recrystallising the residue from diethyl ether/ligroin, there
  7. customare obtained 6.4 g

Sources & evidence

ORD record
ord-288619533ac141d598d088d08ccec5c9
Source dataset
uspto-grants-1990_03
Patent number
US04906666

Reaction notes

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