Sodium Bicarbonate → 1-Hydroxy-5-methoxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexene-1-yl)-2,6,8-nonatriene

HRID 1596028Notes

Reaction equation

[OH:1][CH2:2][CH:3]=[C:4]([CH3:22])[CH2:5][CH:6]([OH:21])[CH:7]=[C:8]([CH3:20])[CH:9]=[CH:10][C:11]1[C:16]([CH3:18])([CH3:17])[CH2:15][CH2:14][CH2:13][C:12]=1[CH3:19].[C:23](=O)(O)[O-].[Na+]>CO>[OH:1][CH2:2][CH:3]=[C:4]([CH3:22])[CH2:5][CH:6]([O:21][CH3:23])[CH:7]=[C:8]([CH3:20])[CH:9]=[CH:10][C:11]1[C:16]([CH3:17])([CH3:18])[CH2:15][CH2:14][CH2:13][C:12]=1[CH3:19]

Participants

Conditions

Temperature: 0 °C

Procedure

1.52 g (5 mmol) of 1,5-dihydroxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexene-1-yl)-2,6,8-nonatriene (I) was dissolved in 20 ml of methanol and the mixture was cooled to 0° C. To the mixture was then added 47.6 mg (0.25 mmol) of paratoluenesulfonic acid hydrate. After the mixture was stirred at 0° C. for 3 hours, a saturated aqueous sodium bicarbonate solution was added to the mixture and the resulting mixture was subjected to extraction with ether, followed by washing with a saturated brine. The resulting product was dried over anhydrous magnesium sulfate and the solvent was evaporated to obtain 1-hydroxy-5-methoxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexene- 1-yl) -2,6,8-nonatriene (IV) as a mixture of E and Z isomers in a yield of 85%.

Workup

extractionthe resulting mixture was subjected to extraction with ether
washby washing with a saturated brine
dry with materialThe resulting product was dried over anhydrous magnesium sulfate
customthe solvent was evaporated

Sources & evidence

ORD record: ord-cad921cf652e4f749cf15ee98cbbb306
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288283B1

Reaction notes

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