Water → HCID 70394574, compound

HRID 1761750Notes

Reaction equation

HRID 1761750 reaction equation
[CH3:1]/[C:2](/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:16])/[CH2:10][CH2:11][CH2:12][C:13]([CH3:15])=[CH2:14])=[CH:3]/[CH2:4][OH:5].[C:17]1(C)C=[CH:21][C:20](S(O)(=O)=O)=[CH:19][CH:18]=1.[OH2:28]>O1C=CCCC1>[CH3:1]/[C:2](/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:16])/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])=[CH:3]/[CH2:4][O:5][CH:21]1[CH2:20][CH2:19][CH2:18][CH2:17][O:28]1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 86742983HCID 86742983, compound

Product 1

HCID 70394574HCID 70394574, compound

Reagents, catalysts & solvents 1

HCID 80803,4-dihydro-2H-pyranSolvent

Procedure

A solution of 1 g (0.0045 mol) (2Z,6E)-3,7,11-trimethyl-2,6,11-dodecatrien-1-ol in 32 ml of 3,4-dihydro-2H-pyran is treated at 0° with 91 mg of p-toluenesulfonic acid. The solution is stirred at the same temperature for 2 hours under argon. After the addition of 100 ml of water the mixture is extracted with ether. The organic phase is washed with sodium bicarbonate solution. After drying and removing the solvent the residue is chromatographed on silica gel with ether-hexane 1:1. There is obtained tetrahydro-2-[[(2Z,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyl]oxy]-2H-pyran which has the following bands in the IR spectrum: 1666 cm-1, 1444 cm-1, 1379 cm-1, 1116 cm-1, 1075 cm-1, 1020 cm-1.

Workup

  1. extractionis extracted with ether
  2. washThe organic phase is washed with sodium bicarbonate solution
  3. customAfter drying
  4. customremoving the solvent the residue
  5. customis chromatographed on silica gel with ether-hexane 1:1

Sources & evidence

ORD record
ord-fbb254b4dec246149af41d90cec6b058
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

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