Water → HCID 86742989, compound

HRID 1761764Notes

Reaction equation

HRID 1761764 reaction equation
[CH3:1][C:2]([CH:4]([OH:23])[CH2:5][CH2:6]/[C:7](/C)=[CH:8]\[CH2:9][CH2:10]/[C:11](/C)=[CH:12]\[CH2:13][O:14]C1CCCCO1)=C.O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(=O)(O)[O-].[Na+]>O1CCCC1.CCOCC>[CH2:1]=[CH:2][CH:4]([OH:23])[CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][OH:14]

Participants

7

Reactant 4

HCID 962Water2×HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 21242304HCID 21242304, compound

Product 1

HCID 86742989HCID 86742989, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.5 g (0.0016 mol) of (6Z,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 (6Z,10Z)-1,6,10-dodecatriene-3,12-diol which has the following bands in the IR spectrum: 3448 cm-1, 1646 cm-1, 1443 cm-1, 1375 cm-1, 998 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-0be0235dbc8e44c6be174cf6fd8e392e
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

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