Water → HCID 67326033, compound

HRID 1516950Notes

Reaction equation

HRID 1516950 reaction equation
[CH3:1][C:2]1[CH2:11][CH:10]=[C:9]2[C:4]([CH3:14])([CH2:5][CH2:6][CH2:7][C:8]2([CH3:13])[CH3:12])[C:3]=1[CH2:15][CH:16]=[O:17].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>CCOCC>[CH3:1][C:2]1[CH2:11][CH:10]=[C:9]2[C:4]([CH3:14])([CH2:5][CH2:6][CH2:7][C:8]2([CH3:12])[CH3:13])[C:3]=1[CH2:15][CH2:16][OH:17]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 75079484HCID 75079484, compound

Product 1

HCID 67326033HCID 67326033, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of (2,5,5,8a-tetramethyl-3,5,6,7,8,8a-hexahydro-1-naphthalenyl)acetaldehyde obtained in step A) (3.40 g; 14.2 mmol) in Et2O (10 ml) was added drop-wise to a stirred suspension of LiAlH4 (410 mg; 10.7 mmol) in Et2O (20 ml) at such a rate that a gentle reflux was maintained (5 minutes). The suspension was heated at reflux for 30 minutes, cooled at 0° C. and treated successively drop-wise with water (0.4 ml), 5% aqueous NaOH (0.4 ml) and water (3×0.4 ml). After stirring for 5 minutes at room temperature the suspension was filtered over Celite and the filtrate concentrated. Bulb-to-bulb distillation (130° C. (oven temp.)/0.03 mbar) afforded pure 2-(2,5,5,8a-tetramethyl-3,5,6,7,8,8a-hexahydro-1-naphthalenyl)ethanol (1) (3.21 g; yield=90%).

Workup

  1. temperaturea gentle reflux
  2. temperaturewas maintained (5 minutes)
  3. temperatureThe suspension was heated
  4. temperatureat reflux for 30 minutes
  5. additiontreated successively
  6. filtrationwas filtered over Celite
  7. concentrationthe filtrate concentrated
  8. distillationBulb-to-bulb distillation (130° C. (oven temp.)/0.03 mbar)

Sources & evidence

ORD record
ord-cfba41bb485345ddab6cc76dd3ffdcb9
Source dataset
uspto-grants-2012_07
Patent number
US08227630B2

Reaction notes

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