3,4-dihydro-2H-pyran → 4-{[6-(tetrahydro-2H-pyran-2-yloxy)hexyl]oxy}benzenecarboxylic acid

HRID 424315Notes

Reaction equation

HRID 424315 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[OH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)C>[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 36284134-(6-Hydroxyhexyloxy)benzoic acid

Product 1

HCID 33581684-{[6-(tetrahydro-2H-pyran-2-yloxy)hexyl]oxy}benzenecarboxylic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 3,4-Dihydro-2H-pyran (24.7 g) was added drop wise at room temperature to a solution of 4[(6-hydroxyhexyl)oxy]benzoic acid (35 g), toluene-4-sulfonic acid monohydrate (1.8) in diethylether (440 ml) and stirred at room temperature for 18 h. The resulting mixture was filtered over Hyflo Super Cel (FLUKA), organic solvents were removed in vacuum. The residue (60 g) was purified by column flash chromatography on silica gel using toluene/ethyl acetate (1:1) as eluent, to give after crystallisation from ethyl acetate/hexane (5:40) 4{[6(tetrahydro-2H-pyran-2-yloxy)hexyl]oxy}benzoic acid.

Workup

  1. filtrationThe resulting mixture was filtered over Hyflo Super Cel (FLUKA), organic solvents
  2. customwere removed in vacuum
  3. customThe residue (60 g) was purified by column flash chromatography on silica gel
  4. customto give
  5. customafter crystallisation from ethyl acetate/hexane (5:40) 4{[6(tetrahydro-2H-pyran-2-yloxy)hexyl]oxy}benzoic acid

Sources & evidence

ORD record
ord-d375de1fcf174d44a2b2c3cccc14ae87
Source dataset
uspto-grants-2012_01
Patent number
US08105662B2

Reaction notes

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