Chlorosulfonic acid → 5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthalenesulfonyl chloride

HRID 2256849Notes

Reaction equation

HRID 2256849 reaction equation
[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH3:13])([CH3:12])[CH2:4][CH2:3]1.[Cl:15][S:16](O)(=[O:18])=[O:17]>>[CH3:1][C:2]1([CH3:14])[CH2:3][CH2:4][C:5]([CH3:13])([CH3:12])[C:6]2[CH:7]=[C:8]([S:16]([Cl:15])(=[O:18])=[O:17])[CH:9]=[CH:10][C:11]1=2

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 811861,1,4,4-Tetramethyltetralin

Product 1

HCID 27954675,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthalenesulfonyl chloride

Conditions

Temperature
60 °C

Procedure

94.0 g (0.5 mol) of 1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene were stirred into 100 ml of chlorosulfonic acid at 20° C. within 30 min. The reaction solution was maintained at 60° C. for 1 hour, cooled to room temperature and then poured into 1.5 1 of ice and extracted with ether. The organic phase was washed to neutrality with brine and water, dried over magnesium sulfate and evaporated under reduced pressure. Recrystallization of the residue from methanol yielded 55.0 g of 5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-sulfonyl chloride of melting point 71°-74° C.

Workup

  1. temperaturecooled to room temperature
  2. additionpoured into 1.5 1 of ice
  3. extractionextracted with ether
  4. washThe organic phase was washed
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customRecrystallization of the residue from methanol

Sources & evidence

ORD record
ord-54a89dada2fa4fd3bb4c62e8f871c9ae
Source dataset
uspto-grants-1997_08
Patent number
US05656619

Reaction notes

Loading…