Thionyl Chloride → 6-Benzenesulfonyl-1-chloro-1,2,3,4-tetrahydro-naphthalene

HRID 1452472Notes

Reaction equation

HRID 1452472 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16](O)[CH2:15][CH2:14][CH2:13]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:23])=O>C1(C)C=CC=CC=1>[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]([Cl:23])[CH2:15][CH2:14][CH2:13]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 575267796-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-ol

Product 1

HCID 575267806-Benzenesulfonyl-1-chloro-1,2,3,4-tetrahydro-naphthaleneYield 86.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-ol (0.65 g, 2.26 mmol) was dissoved in 50 mL toluene, and 1 mL of thionyl chloride was added. The reaction was refluxed for one hour, and then cooled. Solvent was removed under reduced pressure to yield 6-benzenesulfonyl-1-chloro-1,2,3,4-tetrahydro-naphthalene (0.6 g, 86.3%) as a crude oil. MS: 308 (M+H)+.

Workup

  1. temperatureThe reaction was refluxed for one hour
  2. temperaturecooled
  3. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ac58d38312f6424f96277e9a5b576c0b
Source dataset
uspto-grants-2009_01
Patent number
US07473690B2

Reaction notes

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