Potassium Hydroxide → HCID 22035731, compound

HRID 1790795Notes

Reaction equation

HRID 1790795 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[OH-].[K+].[CH3:15][O:16][C:17]1[CH:24]=[CH:23]C(CCl)=[CH:19][CH:18]=1>C(O)C>[OH:1][CH:2]1[CH2:3][CH2:4][CH:5]([C:8]([O:10][CH2:11][C:12]2[CH:23]=[CH:24][C:17]([O:16][CH3:15])=[CH:18][CH:19]=2)=[O:9])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 699934-Methyloxybenzyl chlorideHCID 86973Ethyl 4-hydroxycyclohexanecarboxylate

Product 1

HCID 22035731HCID 22035731, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of ethyl 4-hydroxycyclohexanoate (8.61 g, 50 mmole) in 50 ml ethanol was added a solution of potassium hydroxide 85% (3.63 g, 55 mmole) and the mixture was stirred for 6 hours at 70° C. The mixture was evaporated under reduced pressure, coevaporated two times with N,N-dimethylformamide and reduced to about 100 ml. 4-Methoxybenzyl chloride (9.4 g, 60 mmole) was added and the mixture was stirred for 18 hours at 60° C. The mixture was evaporated under reduced pressure and 250 ml ethyl acetate was added. The organic phase was washed five times with water, dried with sodiun sulfate and evaporated under reduced pressure. Yield: 13.2 g=100% (crude)

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. stirringthe mixture was stirred for 18 hours at 60° C
  3. customThe mixture was evaporated under reduced pressure and 250 ml ethyl acetate
  4. additionwas added
  5. washThe organic phase was washed five times with water
  6. dry with materialdried with sodiun sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9d12840f41c2495088230f709298611a
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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