Acetaldehyde → HCID 20575444, compound

HRID 894366Notes

Reaction equation

HRID 894366 reaction equation
[Li].C([Li])CCC.[CH:7]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[CH:18](=[O:20])[CH3:19]>CCCCCC.C(NC(C)C)(C)C>[OH:20][CH:18]([C:7]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)[CH3:19]

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 18686Ethyl cyclohexanoateHCID 3028194LithiumHCID 178418339Butyllithium

Product 1

HCID 20575444HCID 20575444, compound

Reagents, catalysts & solvents 2

HCID 7912DiisopropylamineSolventHCID 8058HexaneSolvent

Procedure

A solution of lithium isopropylamidide was prepared from 300 cm3 butyl lithium 1.5 M in hexane and 52 g of diisopropylamine. At -40° C. 62.4 g (0.4 mole) of ethyl cyclohexyl-carboxylate were added, then at -80° C. 17.6 g of acetaldehyde were also added. The solvent was evaporated off and the mixture was poured into acid ice water. After extraction with benzene the ether was distilled off and a colourless liquid was obtained.

Workup

  1. customAt -40° C
  2. customat -80° C
  3. customThe solvent was evaporated off
  4. additionthe mixture was poured into acid ice water
  5. extractionAfter extraction with benzene the ether
  6. distillationwas distilled off
  7. customa colourless liquid was obtained

Sources & evidence

ORD record
ord-a163e5de1da342db949f11cec61f5888
Source dataset
uspto-grants-1981_08
Patent number
US04283420

Reaction notes

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