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

HRID 2247900Notes

Reaction equation

HRID 2247900 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 3,4-dihydro-2H-pyran, 0.28 parts of dichloromethane and 300 parts of 4-methylbenzenesulfonic acid was stirred and for 2 hours at reflux temperature. After cooling, there was added Na2CO3 and the whole was stirred for 10 min. The reaction mixture was filtered and the filtrate was evaporated. The residue was co-evaporated with methylbenzene and was further 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. 54).

Workup

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

Sources & evidence

ORD record
ord-b4fe47820f264a55b9758178993e28f1
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

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