Diethyl Ether → Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol

HRID 866545Notes

Reaction equation

HRID 866545 reaction equation
C[O:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2)=O.CCOCC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O>[OH:2][CH2:3][C:5]12[CH2:14][CH:9]3[CH2:8][CH:7]([CH2:13][CH:11]([CH2:10]3)[CH2:12]1)[CH2:6]2

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 136553Tricyclo(3.3.1.13,7)decane-1-carboxylic acid, methyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl-1-adamantanecarboxylate (104 gm.) dissolved in 465 ml. anhydrous ether was added over a 2 hour period to 37.5 gm. lithium aluminum hydride in 753 ml. anhydrous ether. The mixture was stirred an additional 2 hours, cooled and water added gradually. The ether was separated. The water was extracted twice with ether and the combined ether layers dried and concentrated. The residual solid was dissolved in methanol and water was added to precipitate the product which was filtered and dried over P2O5 to give 80 gm., m.p. 113.5°-15.5°.

Workup

  1. temperaturecooled
  2. customThe ether was separated
  3. extractionThe water was extracted twice with ether
  4. dry with materialthe combined ether layers dried
  5. concentrationconcentrated
  6. dissolutionThe residual solid was dissolved in methanol
  7. additionwater was added
  8. customto precipitate the product which
  9. filtrationwas filtered
  10. dry with materialdried over P2O5
  11. customto give 80 gm

Sources & evidence

ORD record
ord-019ff87fe3ea4b1294793710b678bd11
Source dataset
uspto-grants-1978_07
Patent number
US04100170

Reaction notes

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