Potassium Hydroxide → HCID 22035731, compound

HRID 989974Notes

Reaction equation

HRID 989974 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 sodium 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 sodium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b31d7b9d4bc04701b7c7c2241a64ed19
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

Loading…