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

HRID 617853Notes

Reaction equation

HRID 617853 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-8bcd38f1c0c64b6e8a924378f1d696a6
Source dataset
uspto-grants-1999_09
Patent number
US05952316

Reaction notes

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