Sodium Hydroxide → HCID 75079484, compound

HRID 1516947Notes

Reaction equation

HRID 1516947 reaction equation
[C:1]([C:3]1(O)[C:12]2([CH3:13])[C:7]([C:8]([CH3:15])([CH3:14])[CH2:9][CH2:10][CH2:11]2)=[CH:6][CH2:5][CH:4]1[CH3:16])#[CH:2].[OH-:18].[Na+]>CC1C=CC=CC=1C>[CH3:16][C:4]1[CH2:5][CH:6]=[C:7]2[C:12]([CH3:13])([CH2:11][CH2:10][CH2:9][C:8]2([CH3:15])[CH3:14])[C:3]=1[CH2:1][CH:2]=[O:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 76782947HCID 76782947, compound

Product 1

HCID 75079484HCID 75079484, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
145 °C

Procedure

A solution of 1-ethynyl-2,5,5,8a-tetramethyl-1,2,3,5,6,7,8,8a-octahydro-1-naphthalenol (4.00 g; 17.2 mmol) in o-xylene (60 ml) was treated with [V2O6SiPh2]n (400 mg) [Tetrahedron Lett. 1976, 17, 2981] and heated at reflux (145° C.). After 17 hours, the rearrangement was complete. The reaction mixture was poured into 5% aquous NaOH. The product was extracted twice with Et2O and washed successively with H2O and twice with satured aqueous NaCl, dried (Na2SO4) and evaporated. Bulb-to-bulb distillation (125° C. (oven temp.)/0.04 mbar) afforded 97% pure (2,5,5,8a-tetramethyl-3,5,6,7,8,8a-hexahydro-1-naphthalenyl)acetaldehyde (3.42 g; yield=83%).

Workup

  1. temperatureheated
  2. extractionThe product was extracted twice with Et2O
  3. washwashed successively with H2O and twice with satured aqueous NaCl
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. distillationBulb-to-bulb distillation (125° C. (oven temp.)/0.04 mbar)

Sources & evidence

ORD record
ord-cf279395eb5c43f5ae197b78d551ea9a
Source dataset
uspto-grants-2012_07
Patent number
US08227629B2

Reaction notes

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