2-Chloroethanol → o-(beta-Hydroxyethoxy)-thioanisole

HRID 1580300Notes

Reaction equation

HRID 1580300 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH3:9].[O-:10][CH2:11][CH3:12].[Na+].OCCCl>C(O)C>[OH:10][CH2:11][CH2:12][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH3:9]

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 61261o-(Methylthio)phenolHCID 2723922Sodium ethoxide

Product 1

HCID 22036270o-(beta-Hydroxyethoxy)-thioanisole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

o-Hydroxythioanisole (14.1 g., 0.1 mole) is dissolved in sodium ethoxide (6.8 g., 0.1 mole) in absolute ethanol (100 ml.) and stirred as β-hydroxyethyl chloride (8.1 g., 0.1 mole) is added. The reaction mixture is refluxed for 2 hours and cooled. The o-(β-hydroxyethoxy)-thioanisole is extracted.

Workup

  1. additionis added
  2. temperatureThe reaction mixture is refluxed for 2 hours
  3. temperaturecooled
  4. extractionThe o-(β-hydroxyethoxy)-thioanisole is extracted

Sources & evidence

ORD record
ord-5316a52c36a048fdaa525ded247bf4f2
Source dataset
uspto-grants-1976_01
Patent number
US03932498

Reaction notes

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