Water → HCID 86742984, compound

HRID 1761752Notes

Reaction equation

HRID 1761752 reaction equation
[CH3:1][C:2]([CH:4]([OH:23])[CH2:5][CH2:6]/[C:7](/[CH3:22])=[CH:8]/[CH2:9][CH2:10]/[C:11](/[CH3:21])=[CH:12]\[CH2:13][O:14]C1CCCCO1)=[CH2:3].O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(=O)(O)[O-].[Na+]>O1CCCC1.CCOCC>[CH3:3][C:2]([CH:4]([OH:23])[CH2:5][CH2:6]/[C:7](/[CH3:22])=[CH:8]/[CH2:9][CH2:10]/[C:11](/[CH3:21])=[CH:12]\[CH2:13][OH:14])=[CH2:1]

Participants

7

Reactant 4

HCID 962Water2×HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 70393861HCID 70393861, compound

Product 1

HCID 86742984HCID 86742984, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.5 g (0.0016 mol) of (6E,10Z)-2,6,10-trimethyl-12-[(tetrahydro-2H-pyran-2-yl)oxy]-1,6,10-dodecatrien-3-ol dissolved in 14.5 ml of tetrahydrofuran and 3.7 ml of water is treated with 167.2 mg (0.4 mol equivalents) of pyridinium p-toluenesulfonate. The solution is boiled at reflux for 17 hours. After cooling 100 ml of water and 300 ml of ether are added thereto. The organic phase is neutralized 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 (6E,10Z)-2,6,10-trimethyl-1,6,10-dodecatriene-3,12-diol which has the following bands in the IR spectrum: 3344 cm-1, 1647 cm-1, 1449 cm-1, 1375 cm-1, 997 cm-1.

Workup

  1. temperatureat reflux for 17 hours
  2. additionare added
  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-b4d5ea3e1ca445f494eca98252431d31
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

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