Diethyl Ether → HCID 57437803, compound

HRID 1264641Notes

Reaction equation

HRID 1264641 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.[H-].[Na+].[N+:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22](Cl)(=[O:24])=[O:23])([O-:15])=[O:14].CCO[CH2:29][CH3:30]>O1CCCC1.O>[N+:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22]([O:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][O:8][S:22]([C:30]2[CH:29]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:13]([O-:15])=[O:14])(=[O:24])=[O:23])=[CH:4][CH:3]=1)(=[O:24])=[O:23])([O-:15])=[O:14]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 10393TyrosolHCID 155402-Nitrobenzenesulfonyl chlorideHCID 24758Sodium hydride

Product 1

HCID 57437803HCID 57437803, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2.76 g (20 mmol) of 4-hydroxyphenethyl alcohol in 70 mL of anhydrous tetrahydrofuran at rt was added 4.8 g (200 mmol) of sodium hydride (95%, dry powder). After stirring at rt for 10 min, 18.5 g (80 mmol) of 2-nitrobenzenesulfonyl chloride was added. After the resulting mixture was stirred at rt for 16 h, 250 mL of ether was added. The mixture was cooled to 0° C. and water was slowly added to the the mixture to quench excess sodium hydride. After quenching process was completed, additional 300 mL of water was added. The resulting precipitate was collected via filtration, washed with water and dried in vacuo to yield 2-nitrobenzenesulfonic acid 2-[4-(2-nitrobenzenesulfonyloxy)-phenyl]-ethyl ester as a white powder (9.13 g, 90%): MS (ESI) 509 [M+H]+.

Workup

  1. stirringAfter the resulting mixture was stirred at rt for 16 h
  2. temperatureThe mixture was cooled to 0° C.
  3. customto quench excess sodium hydride
  4. customAfter quenching process
  5. additionadditional 300 mL of water was added
  6. filtrationThe resulting precipitate was collected via filtration
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-6e0952bc800b49b4b785d2ddcdcb95d4
Source dataset
uspto-grants-2003_04
Patent number
US06544992B1

Reaction notes

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