3,4-dihydro-2H-pyran → Dodecanediol monotetrahydropyranyl ether

HRID 862830Notes

Reaction equation

HRID 862830 reaction equation
[CH:1]([OH:14])([OH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[O:15]1[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16]1.C(N(CC)CC)C>O1CCCC1.ClCCl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[O:14][CH:1]([OH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 8471TriethylamineHCID 181638Dodecanediol

Product 1

HCID 21849359Dodecanediol monotetrahydropyranyl etherYield 25%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dodecanediol (23.000 g) was dissolved in 230 ml of dry tetrahydrofuran and 40 ml of dichloromethane, and 10 mg of p-toluenesulfonic acid and 9,578 g of dihydropyran were added thereto. The mixture was stirred at room temperature for a day. Triethylamine (1.0 ml) was added thereto to stop the reaction and the reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 8.132 g of dodecanediol monotetrahydropyranyl ether.

Workup

  1. customthe reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-799cc51deed34b8cae665cd944f46224
Source dataset
uspto-grants-1998_02
Patent number
US05719176

Reaction notes

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