Water → HCID 178444475, compound

HRID 246790Notes

Reaction equation

HRID 246790 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C@H:12]1[CH2:17][CH2:16][C@H:15]([CH2:18][CH2:19][C:20](OCC)=[O:21])[CH2:14][CH2:13]1)[CH2:8][CH2:9][CH2:10][CH3:11].O.S(=O)(=O)(O)O>C(OCC)C>[CH2:7]([C@H:12]1[CH2:13][CH2:14][C@H:15]([CH2:18][CH2:19][CH2:20][OH:21])[CH2:16][CH2:17]1)[CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 21226445Aluminium lithium hydrideHCID 178444480HCID 178444480, compound

Product 1

HCID 178444475HCID 178444475, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

250 ml of absolute diethyl ether were placed in a sulphonation flask under nitrogen gasification and treated cautiously with 3.9 g of lithium aluminium hydride. A solution of 46.9 g of ethyl β-(trans-4-pentylcyclohexyl)propionate in 200 ml of absolute diethyl ether was added dropwise thereto within 50 minutes. A further 250 ml of absolute diethyl ether were then added thereto and the mixture was stirred overnight. Subsequently, there were added dropwise to the mixture within 10 minutes 21 ml of water and then 210 ml of 10% sulphuric acid. The aqueous phase was separated and extracted twice with diethyl ether. The combined organic phases were washed once with water and once with saturated sodium chloride solution, dried over sodium sulphate and evaporated. 39.2 g of 3-(trans-4-pentylcyclohexyl)-1-propanol were obtained as a colourless oil.

Workup

  1. customThe aqueous phase was separated
  2. extractionextracted twice with diethyl ether
  3. washThe combined organic phases were washed once with water and once with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-e27bc3d142c54b8195527fe5d891e584
Source dataset
uspto-grants-1987_11
Patent number
US04704005

Reaction notes

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