2-Mercaptoethanol → HCID 13885751, compound

HRID 1493882Notes

Reaction equation

HRID 1493882 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. 1 M sodium methylate solution. Subsequently, 9.39 g. 3-(4-acetyl-3-hydroxy-2-propyl-phenoxy)-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 2 M aqueous sodium hydroxide solution and with 2 M 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-794f31817b0c49e49fb4b5b8a450ff33
Source dataset
uspto-grants-1991_06
Patent number
US05025028

Reaction notes

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