Hydrochloric Acid → (4-Pentylcyclohexyl)methanol

HRID 342321Notes

Reaction equation

HRID 342321 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[CH2:7]([CH:12]1[CH2:17][CH2:16][CH:15]([C:18](Cl)=[O:19])[CH2:14][CH2:13]1)[CH2:8][CH2:9][CH2:10][CH3:11].Cl>CCOCC>[CH2:7]([CH:12]1[CH2:13][CH2:14][CH: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 12653189Cyclohexanecarbonyl chloride, 4-pentyl-, trans-HCID 21226445Aluminium lithium hydride

Product 1

HCID 13548135(4-Pentylcyclohexyl)methanolYield 96.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a dispersion of 1.75 g of aluminum lithium hydride in 40 ml of dry ether, a solution of 10 g of 4-n-pentylcyclohexanecarbonyl chloride in 12 ml of ether was added dropwise below 5° C., followed by stirring overnight at room temperature. After the reaction, the reaction mixture was acidified with 5%-hydrochloric acid aqueous solution until a pH value of 1 were shown and was subjected to extraction with ether. The organic layer was washed successively with water, 5%-sodium hydroxide, and water, followed by drying with anhydrous magnesium sulfate. The resultant organic layer was subjected to filtration, followed by distilling-off of the solvent to obtain 8.2 g of 4-n-pentylcyclohexylmethanol.

Workup

  1. customAfter the reaction
  2. extractionwas subjected to extraction with ether
  3. washThe organic layer was washed successively with water, 5%-sodium hydroxide, and water
  4. dry with materialby drying with anhydrous magnesium sulfate
  5. filtrationThe resultant organic layer was subjected to filtration

Sources & evidence

ORD record
ord-aaa0cc5aff1e4815bc3e2c76b2897c4b
Source dataset
uspto-grants-1999_01
Patent number
US05858269

Reaction notes

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