4-Toluenesulfonyl chloride → HCID 11313625, compound

HRID 413013Notes

Reaction equation

HRID 413013 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[Na+].[CH2:25]([O:32][C:33]1[CH:38]=[CH:37][C:36](O)=[CH:35][CH:34]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(#N)C>[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:36]1[CH:37]=[CH:38][C:33]([O:32][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:34][CH:35]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 7638MonobenzoneHCID 121412-(Benzyloxy) ethanolHCID 14798Sodium Hydroxide

Product 1

HCID 11313625HCID 11313625, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(Benzyloxy)ethanol (61.0 g, 0.4 mole, and p-toluenesulfonyl chloride (80.0 g, 0.4 mole) were added with stirring to acetonitrile (20 ml) in a litre, four-necked, round-bottom flask, equipped with a mechanical stirrer, reflux condenser, thermometer and a dropping funnel. Aqueous sodium hydroxide (40.0 g, 1.0 mole/80 ml of water) was added slowly from the dropping funnel while the temperature of the reaction mixture was kept below 55° C. After the addition was complete, the reaction mixture was stirred for one hour as it cooled to room temperature. Then, 4-(benzyloxy)phenol (80.0 g, 0.4 mole) was added and the reaction mixture (OV-1 column, 100° C. for 2 minutes, 25° C./min to 300° C. showed that the reaction was complete.

Workup

  1. customfour-necked, round-bottom flask, equipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. customwas kept below 55° C
  4. additionAfter the addition
  5. waitthe reaction mixture (OV-1 column, 100° C. for 2 minutes

Sources & evidence

ORD record
ord-9e28758f54fa464a949fe004ab528528
Source dataset
uspto-grants-2003_05
Patent number
US06566301B2

Reaction notes

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