p-Toluenesulfonic acid → 2-[(5-chloro-2-nitrophenyl)methoxy]tetrahydro-2H-pyran

HRID 1588072Notes

Reaction equation

HRID 1588072 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH2:8][OH:9])[CH:7]=1.[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1.CC1C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH2:8][O:9][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][O:13]2)[CH:7]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 10340Sodium CarbonateHCID 5560665-Chloro-2-nitrobenzyl alcohol

Product 1

HCID 151770832-[(5-chloro-2-nitrophenyl)methoxy]tetrahydro-2H-pyranYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 25 parts of 5-chloro-2-nitrobenzenemethanol, 13.3 parts of dihydro-2H-pyran, 300 parts of dichloromethane and 0.28 parts of 4-methylbenzenesulfonic acid was stirred for 2 hours at reflux temperature. After cooling, the reaction mixture was neutralized with sodium carbonate and stirred for 10 min. The whole was filtered and the filtrate was evaporated. The residue was co-evaporated with methylbenzene and then purified by column chromatography (silica gel; CHCl3). The eluent of the desired fraction was evaporated and the residue was co-evaporated with methylbenzene, yielding 36 parts (99.6%) of 2-[(5-chloro-2-nitrophenyl)methoxy]tetrahydro-2H-pyran (interm. 1).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. stirringstirred for 10 min
  4. filtrationThe whole was filtered
  5. customthe filtrate was evaporated
  6. custompurified by column chromatography (silica gel; CHCl3)
  7. customThe eluent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-7839fed7d8824c5fbf9932840ddb90c9
Source dataset
uspto-grants-1993_06
Patent number
US05220023

Reaction notes

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