4-Toluenesulfonyl chloride → HCID 21387572, compound

HRID 1833861Notes

Reaction equation

HRID 1833861 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([C:12]1[O:13][CH:14]=[CH:15][CH:16]=1)(O)[CH3:10].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>N1C=CC=CC=1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([C:12]1[O:13][CH:14]=[CH:15][CH:16]=1)=[CH2:10]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 21387530HCID 21387530, compound

Product 1

HCID 21387572HCID 21387572, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(±) 1-(2,3-Dichlorophenyl)-1-(2-furyl)ethanol (92 g.) was heated on a steam bath in pyridine (250 ml.) containing p-toluenesulphonyl chloride (69 g.) for 1 hour. The solution was poured into ice water (1 liter) and extracted with diethyl ether (5 × 500 ml.). The combined ethereal extracts were washed with water (2 × 500 ml.), dried over sodium sulphate, filtered and evaporated to give a dark oil, which was distilled to give 1-(2,3-dichlorophenyl)-1-(2-furyl)ethylene as a pale yellow liquid (46 g.), b.p. 140°-180° C./20 mm.Hg.

Workup

  1. extractionextracted with diethyl ether (5 × 500 ml.)
  2. washThe combined ethereal extracts were washed with water (2 × 500 ml.)
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customto give a dark oil, which
  7. distillationwas distilled

Sources & evidence

ORD record
ord-ecd4a07ce621476dbae6310a1d2652e3
Source dataset
uspto-grants-1978_01
Patent number
US04067723

Reaction notes

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