Hydrochloric Acid → 2-(1H-Inden-3-yl)ethyl 4-methylbenzenesulphonate

HRID 260666Notes

Reaction equation

HRID 260666 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][OH:12])=[CH:2]1.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.Cl>N1C=CC=CC=1>[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([O:12][CH2:11][CH2:10][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:1][CH:2]=2)(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 113556481H-Indene-3-ethanol

Product 1

HCID 121780952-(1H-Inden-3-yl)ethyl 4-methylbenzenesulphonateYield 71.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5 g (0.031 mol) of 1H-indene-3-ethanol are dissolved in 50 ml of dry pyridine. The mixture is stirred and cooled using an ice bath, 5.9 g (0.031 mol) of 4-methylbenzenesulphonyl chloride are added in portions, and stirring is continued under cold conditions for 1 h and then at room temperature for 4 h. The solution obtained is poured into a mixture of 100 ml of 10N hydrochloric acid and 200 g of ice. The mixture is extracted twice with diethyl ether, and the organic phase is separated, washed with water, dried over magnesium sulphate and filtered. The filtrate is evaporated under reduced pressure. 7 g of an oily product are obtained which is used as it is in the following step.

Workup

  1. temperaturecooled
  2. stirringstirring
  3. waitat room temperature for 4 h
  4. customThe solution obtained
  5. extractionThe mixture is extracted twice with diethyl ether
  6. customthe organic phase is separated
  7. washwashed with water
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. customThe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-88934561421c4dcca73a81f1e7b58d0e
Source dataset
uspto-grants-1996_06
Patent number
US05530002

Reaction notes

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