Chlorosulfonic acid → HCID 22000916, compound

HRID 1976298Notes

Reaction equation

HRID 1976298 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH3:6][C:7]1([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:16][CH2:15][C:14]2[C:9](=[C:10]([CH3:19])[C:11]([CH3:18])=[CH:12][C:13]=2[CH3:17])[O:8]1.C(=O)([O-])O.[Na+]>ClCCl>[CH2:24]([O:23][C:21]([CH2:20][C:7]1([CH3:6])[CH2:16][CH2:15][C:14]2[C:9](=[C:10]([CH3:19])[C:11]([CH3:18])=[C:12]([S:2]([Cl:1])(=[O:5])=[O:3])[C:13]=2[CH3:17])[O:8]1)=[O:22])[CH3:25]

Participants

5

Reactant 3

HCID 24638Chlorosulfonic acidHCID 516892Sodium BicarbonateHCID 54108263HCID 54108263, compound

Product 1

HCID 22000916HCID 22000916, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of chlorosulfonic acid (2.79 ml) in dichloromethane (CH2Cl2) (15 ml) was added dropwise to a solution of ethyl (2,5,7,8-tetramethylchroman-2-yl)acetate (2.90 g) in CH2Cl2 (100 ml) at 0-10° C. over an hour. After stirring at room temperature for 5 hours, the reaction mixture was poured into chilled saturated aqueous sodium hydrogen carbonate (sat. aq. NaHCO3). The separated organic phase was washed with sat. aq. NaHCO3, water, and brine, and dried over MgSO4. After filtration, the filtrate was concentrated under reduced pressure to give 2-ethoxycarbonylmethyl-2,5,7,8-tetramethylchroman-6-sulfonyl chloride as a syrup (3.29 g).

Workup

  1. additionthe reaction mixture was poured
  2. washThe separated organic phase was washed with sat. aq. NaHCO3, water, and brine
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ae3865def126403482015621e79dd42d
Source dataset
uspto-grants-2001_05
Patent number
US06225480B1

Reaction notes

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