Hydrochloric Acid → HCID 178444539, compound

HRID 2231615Notes

Reaction equation

HRID 2231615 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18](O)=[O:19])[CH2:14][CH2:13]1)[CH2:8][CH2:9][CH2:10][CH3:11].Cl>O1CCCC1>[CH2:7]([C@H:12]1[CH2:13][CH2:14][C@H:15]([CH2:18][OH:19])[CH2:16][CH2:17]1)[CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 178444557HCID 178444557, compound

Product 1

HCID 178444539HCID 178444539, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.79 g of lithium aluminium hydride were placed in 100 ml of absolute tetrahydrofuran while gassing with argon and treated within 30 minutes with a solution of 19.83 g of trans-4-pentylcyclohexanecarboxylic acid in 100 ml of absolute tetrahydrofuran. After completion of the addition, the mixture was heated to reflux for 1 hour, then cautiously added to 200 ml of 2N hydrochloric acid and extracted three times with 100 ml of diethyl ether each time. The organic phases were washed with 100 ml of saturated sodium carbonate solution, dried over potassium carbonate and concentrated. Distillation of the residue (19.2 g) gave in the main run 17.7 g (96%) of (trans-4-pentylcyclohexyl)methanol as a colourless oil (purity 99.9%); b.p. 89° C./0.2 mmHg.

Workup

  1. additionAfter completion of the addition
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 1 hour
  4. extractionextracted three times with 100 ml of diethyl ether each time
  5. washThe organic phases were washed with 100 ml of saturated sodium carbonate solution
  6. dry with materialdried over potassium carbonate
  7. concentrationconcentrated
  8. distillationDistillation of the residue (19.2 g)

Sources & evidence

ORD record
ord-19e8df4b5c1046a184b2cf7d8bee2e6a
Source dataset
uspto-grants-1988_11
Patent number
US04783280

Reaction notes

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