Water → HCID 86742984, compound

HRID 1761758Notes

Reaction equation

HRID 1761758 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5](S([O-])(=O)=O)=[CH:4][CH:3]=1.[NH+]1[CH:18]=[CH:17][CH:16]=CC=1.[CH3:19][CH2:20][O:21]CC.C(=O)(O)[O-].[Na+].[O:29]1[CH2:33][CH2:32][CH2:31]C1>>[CH3:18][C:17]([CH:33]([OH:29])[CH2:32][CH2:31]/[C:4](/[CH3:3])=[CH:5]/[CH2:6][CH2:7]/[C:2](/[CH3:12])=[CH:19]\[CH2:20][OH:21])=[CH2:16]

Participants

6

Reactant 5

HCID 962Water2×HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium Bicarbonate

Product 1

HCID 86742984HCID 86742984, compound

Procedure

A solution of 0.5 g (0.0016 mol) of (6Z,10E)-2,6,10-trimethyl-12-[(tetrahydro-H-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. 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: 3346 cm-1, 1649 cm-1, 1446 cm-1, 1377 cm-1, 1001 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-e8fb77c4278141499bf77120bcdf676d
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

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