Red-Al → HCID 69322502, compound

HRID 1926566Notes

Reaction equation

HRID 1926566 reaction equation
COCCO[AlH2-]OCCOC.[Na+].[CH3:13][C:14]1([CH3:29])[CH:19]2[CH2:20][CH:16]([CH2:17][CH2:18]2)[CH:15]1[C:21]1([CH:27]=[O:28])[CH2:26][CH2:25][CH:24]=[CH:23][CH2:22]1>C1(C)C=CC=CC=1>[CH3:13][C:14]1([CH3:29])[CH:19]2[CH2:20][CH:16]([CH2:17][CH2:18]2)[CH:15]1[C:21]1([CH2:27][OH:28])[CH2:26][CH2:25][CH:24]=[CH:23][CH2:22]1

Participants

4

Reactant 2

HCID 16684438Red-AlHCID 86761566HCID 86761566, compound

Product 1

HCID 69322502HCID 69322502, compoundYield 126.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

A 1-L reaction flask equipped with a stirrer, a thermometer, a reflux condenser, a heating mantle, and an addition funnel was charged with Vitride (226 g, 0.73 mol) and toluene (226 g). The resulting mixture was stirred at 20° C. The Diels-Alder product containing 1-(3,3-dimethyl-bicyclo[2.2.1]hept-2-yl)-cyclohex-3-enecarbaldehyde (310 g, 1.32 mol, synthesized as above in EXAMPLE II) was added over about 2 hours. The temperature was allowed to rise to 45° C. The reaction mass was aged for 2.5 hours. The excessive Vitride reagent was quenched with ethyl acetate (CH3CO2CH2CH3, 44 g), followed by sodium hydroxide (NaOH, 25%, 467 g). The temperature was allowed to rise to 50° C. and stirred for another 0.5 hours. The organic phase was diluted with toluene (100 mL), washed with hot water (1 L) twice, and then concentrated to yield the crude product [1-(3,3-dimethyl-bicyclo[2.2.1]hept-2-yl)-cyclohex-3-enyl]-methanol (390 g) having a boiling point of 153° C. at a pressure of 1.7 mmHg.

Workup

  1. customequipped with a stirrer
  2. additionwas added over about 2 hours
  3. customto rise to 45° C
  4. customThe excessive Vitride reagent was quenched with ethyl acetate (CH3CO2CH2CH3, 44 g)
  5. customto rise to 50° C.
  6. stirringstirred for another 0.5 hours
  7. additionThe organic phase was diluted with toluene (100 mL)
  8. washwashed with hot water (1 L) twice
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-64c6a6014cd7469baa9e53af2861ff1b
Source dataset
uspto-grants-2012_05
Patent number
US08183200B1

Reaction notes

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