4-Toluenesulfonyl chloride → HCID 15595486, compound

HRID 986643Notes

Reaction equation

HRID 986643 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:19]=2)([CH2:13]O)[CH2:11]O)=[CH:6][CH:5]=1)[CH3:2].C1(C)C=CC([S:37](Cl)(=O)=O)=CC=1>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH2:15][CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:19]=3)[CH2:13][S:37][CH2:11]2)=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 20156960HCID 20156960, compound

Product 1

HCID 15595486HCID 15595486, compoundYield 161.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent2×

Procedure

2-(4-Ethoxyphenyl)-2-[3-(3-phenoxyphenyl)propyl]propane-1,3-diol (25 g) was dissolved in pyridine (150 ml) and 4-dimethylaminopyridine added (20 mg). p-Toluenesulphonyl chloride (23.4 g), dissolved in pyridine (20 ml), was added dropwise at -5° C. The mixture was allowed to rise to room temperature over 2 hours and stirred overnight. It was then added to a hydrochloric acid-ice mixture, extracted with ether and the extract dried and evaporated to give 40.1 g of crude product which was used without further purification.

Workup

  1. additionwas added dropwise at -5° C
  2. extractionextracted with ether
  3. customthe extract dried
  4. customevaporated

Sources & evidence

ORD record
ord-56515e329c6f40a1b3c82a17608be134
Source dataset
uspto-grants-1987_12
Patent number
US04714710

Reaction notes

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