3,4-dihydro-2H-pyran → HCID 14405876, compound

HRID 1382691Notes

Reaction equation

HRID 1382691 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].[O:16]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17]1>C1COCC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]1[O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14]

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 7903412-Hydroxydodecanoic Acid

Product 1

HCID 14405876HCID 14405876, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

12-Hydroxydodecanoic acid (2.16 g, 10.0 mmol) was suspended in 20mL of dry THF. After the addition of 1.39g (16.5 mmol) of dihydropyran, the solution was stirred for 10 min. at room temperature. Twenty mg (0.105 mmol) of crystalline p-toluenesulfonic acid monohydrate was then added. The mixture became clear immediately, and was stirred for an additional 2 hours at room temperature. Evaporation of solvent under reduced pressure afforded a crude product which was purified by flash chromatography (CHCl3) to yield 2.40 g (80%) of 12-(tetrahydropyranyloxy)dodecanoic acid as a colorless oil.

Workup

  1. stirringwas stirred for an additional 2 hours at room temperature
  2. customEvaporation of solvent under reduced pressure
  3. customafforded a crude product which
  4. customwas purified by flash chromatography (CHCl3)

Sources & evidence

ORD record
ord-812f29986bf74eb89646144ea91d3301
Source dataset
uspto-grants-1989_02
Patent number
US04808480

Reaction notes

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