Water → HCID 21242323, compound

HRID 1761762Notes

Reaction equation

HRID 1761762 reaction equation
[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][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 1549107cis-Farnesol

Product 1

HCID 21242323HCID 21242323, compound

Reagents, catalysts & solvents 1

HCID 80803,4-dihydro-2H-pyranSolvent

Procedure

A solution of 1 g (0.0045 mol) of (2Z,6Z)-3,7,11-trimethyl-2,6,10-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,6Z)-3,7,11-trimethyl-2,6,10-dodecatrienyl]oxy]-2H-pyran which has the following bands in the IR spectrum: 1668 cm-1, 1444 cm-1, 1378 cm-1, 1118 cm-1, 1075 cm-1, 1023 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-16ace29952f34003bdc8a2f1096db521
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

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