Potassium Hydroxide → HCID 54332354, compound

HRID 484984Notes

Reaction equation

HRID 484984 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][C:17]([CH3:25])=[CH:18][CH:19]=[CH:20][C:21]([O:23]C)=[O:22])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C.O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[CH:16][C:17]([CH3:25])=[CH:18][CH:19]=[CH:20][C:21]([OH:23])=[O:22])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 53699862HCID 53699862, compound

Product 1

HCID 54332354HCID 54332354, compoundYield 54.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 7-(4-benzyloxyphenyl)-5-methyl-hepta-2,4,6-trienoate (3.2 g, 9.7 mmol) and potassium hydroxide (1.1 g, 19.4 mmol) in 200 ml of ethanol and 10 ml of water was stirred under nitrogen at room temperature for 48 hrs. The mixture was then concentrated on rotary evaporator and water (250 ml) was added. The solution was extracted with 30 ml of ethyl acetate; the aqueous layer was acidified with 10N HCl to pH 3. The yellow precipitate formed was extracted into ethyl acetate, washed with 30 ml of water, dried (magnesium sulfate) and concentrated on rotary evaporator to give a yellow powder, which was triturated with ethyl acetate to give 1.7 g of the product as yellow powder, mp: 210° C. (sublimed).

Workup

  1. concentrationThe mixture was then concentrated on rotary evaporator and water (250 ml)
  2. additionwas added
  3. extractionThe solution was extracted with 30 ml of ethyl acetate
  4. customThe yellow precipitate formed
  5. extractionwas extracted into ethyl acetate
  6. washwashed with 30 ml of water
  7. dry with materialdried (magnesium sulfate)
  8. concentrationconcentrated on rotary evaporator
  9. customto give a yellow powder, which
  10. customwas triturated with ethyl acetate

Sources & evidence

ORD record
ord-7c8fbf1ec9484be7927090dbbd6d49d2
Source dataset
uspto-grants-1985_08
Patent number
US04534979

Reaction notes

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