Water → (3-Phenylbicyclo[2.2.2]oct-2-en-2-yl)methanol

HRID 247108Notes

Reaction equation

HRID 247108 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]([CH:9]1[CH:14]2[CH2:15][CH2:16][CH:11]([CH2:12][CH2:13]2)[CH:10]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:8].[OH-].[Na+].O>CCOCC>[OH:8][CH2:7][C:9]1[CH:14]2[CH2:15][CH2:16][CH:11]([CH2:12][CH2:13]2)[C:10]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 20161598HCID 20161598, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20161640(3-Phenylbicyclo[2.2.2]oct-2-en-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To lithium aluminium hydride (1 g; 0.03 m) in ether (50 ml) was added 3-formyl-2-phenylbicyclo[2,2,2]octane (4.2 g; 0.02 m) in ether (40 ml) dropwise at 0° C. After 1 hour, 5N sodium hydroxide (1 ml) followed by water (5 ml) was added cautiously. After filtering, the filtrate was evaporated to give an oil which was used directly in (e) below.

Workup

  1. additionwas added cautiously
  2. filtrationAfter filtering
  3. customthe filtrate was evaporated
  4. customto give an oil which

Sources & evidence

ORD record
ord-ff5c61ebe03a4d6f9b61e4ed1aa7e9c3
Source dataset
uspto-grants-1987_11
Patent number
US04705807

Reaction notes

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