Methanol → 65416-26-4

HRID 1462836Notes

Reaction equation

HRID 1462836 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[CH:12]([OH:14])[CH3:13].[H-].[Na+].[CH2:17](Br)[CH3:18].CO>C1C=CC=CC=1.O>[CH3:17][CH2:18][O:14][CH:12](/[CH:11]=[CH:10]/[C:3]1[C:4]([CH3:8])([CH3:9])[CH2:5][CH2:6][CH2:7][C:2]=1[CH3:1])[CH3:13]

Participants

7

Reactant 4

HCID 887MethanolHCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 5373729(3E)-4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-3-buten-2-ol

Product 1

HCID 643699365416-26-4Yield 81.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 350 g (1.8 mol) of β-ionol in 600 ml of benzene was allowed to flow in over a period of 15 minutes to a suspension of 97.5 g (2.34 mol) of sodium hydride (ca 55%-60%) in 3 liters of benzene and the mixture was subsequently stirred at reflux for 8 hours. The mixture was cooled to ca 50° C. and treated over a period of 10 minutes with 232 g (2.13 mol) of ethyl bromide. The mixture was stirred at reflux for 20 hours, cooled to 20° C., cautiously treated with 50 ml of methanol and, after 20 minutes, with 1.2 liters of water. The phases were separated, the organic phase was washed with water until neutral, dried and concentrated. Crude distillation of the crude product gave 326 g of crude ether 2 of boiling point 120°-128° C./10 mmHg. Fine distillation finally gave 274 g (68.3%) of pure and olfactorily good β-ionyl ethyl ether 2 of boiling point 121° C./10 mmHg; nD20 =1.4752.

Workup

  1. temperatureat reflux for 8 hours
  2. temperatureThe mixture was cooled to ca 50° C.
  3. stirringThe mixture was stirred
  4. temperatureat reflux for 20 hours
  5. customThe phases were separated
  6. washthe organic phase was washed with water until neutral,
  7. customdried
  8. concentrationconcentrated
  9. distillationCrude distillation of the crude product

Sources & evidence

ORD record
ord-c4ce314ef6814d89837c2497d4b7828b
Source dataset
uspto-grants-1984_07
Patent number
US04461309

Reaction notes

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