Red-Al → HCID 69323130, compound

HRID 1926567Notes

Reaction equation

HRID 1926567 reaction equation
COCCO[AlH2-]OCCOC.[Na+].[CH3:13][C:14]1([CH3:30])[CH:19]2[CH2:20][CH:16]([CH2:17][CH2:18]2)[CH:15]1[C:21]1([CH:28]=[O:29])[CH2:26][CH2:25][C:24]([CH3:27])=[CH:23][CH2:22]1>C1(C)C=CC=CC=1>[CH3:13][C:14]1([CH3:30])[CH:19]2[CH2:20][CH:16]([CH2:17][CH2:18]2)[CH:15]1[C:21]1([CH2:28][OH:29])[CH2:26][CH2:25][C:24]([CH3:27])=[CH:23][CH2:22]1

Participants

4

Reactant 2

HCID 16684438Red-AlHCID 86761567HCID 86761567, compound

Product 1

HCID 69323130HCID 69323130, compoundYield 82.8%

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 (260 g, 0.84 mol) and toluene (260 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)-4-methyl-cyclohex-3-enecarbaldehyde (275 g, 1.16 mol, synthesized as above in EXAMPLE V) was added over about 2 hours. The temperature was allowed to rise to 40° C. The reaction mass was aged for 3 hours. The excessive Vitride reagent was quenched with ethyl acetate (22 g), followed by sodium hydroxide (25%, 134 g). The temperature was allowed to rise to 50° C. and stirred for another 0.5 hours. The organic phase was washed with hot water (1 L) twice and concentrated to yield the crude product [1-(3,3-dimethyl-bicyclo[2.2.1]hept-2-yl)-4-methyl-cyclohex-3-enyl]-methanol (250 g, 0.96 mol).

Workup

  1. customequipped with a stirrer
  2. additionwas added over about 2 hours
  3. customto rise to 40° C
  4. customThe excessive Vitride reagent was quenched with ethyl acetate (22 g)
  5. customto rise to 50° C.
  6. stirringstirred for another 0.5 hours
  7. washThe organic phase was washed with hot water (1 L) twice
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a068de7ef9fb4df9ab5cf10f0f7f2cc5
Source dataset
uspto-grants-2012_05
Patent number
US08183200B1

Reaction notes

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