1,4-Butanediol → 4-(Tetrahydro-2H-pyran-2-yloxy)-1-butanol

HRID 1271247Notes

Reaction equation

HRID 1271247 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][OH:5].[O:7]1[CH:12]=[CH:11][CH2:10][CH2:9][CH2:8]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl.O1CCCC1>[O:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[O:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:6]

Participants

6

Reactant 3

HCID 80641,4-ButanediolHCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 5591134-(Tetrahydro-2H-pyran-2-yloxy)-1-butanol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 100.0 g of 1,4-butanediol and 20 ml of 3,4-dihydro-2H-pyrane in 80 ml of dichloromethane and 140 ml of tetrahydrofuran, 1.8 g of pyridinium p-toluenesulfonate was added. After stirring at room temperature for 18 hours, the solvent was evaporated under reduced pressure. The residue was extracted three times with diethyl ether after adding saturated brine. After the extract was washed with a small amount of water and dried over anhydrous magnesium sulfate, the solvent was evaporated to obtain 35.98 g of the desired crude product as a colorless oily substance.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. extractionThe residue was extracted three times with diethyl ether
  3. additionafter adding saturated brine
  4. washAfter the extract was washed with a small amount of water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-44b9cf5e8c6e40888a85d7303687e717
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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