Potassium Hydroxide → HCID 86748059, compound

HRID 1742017Notes

Reaction equation

HRID 1742017 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH-].[K+].C1OCCOCCOCCOCCOCCOC1.[CH2:36]([O:38][CH:39]([O:46][CH2:47][CH3:48])[C:40]#[C:41][C:42]([O:44][CH3:45])=[O:43])[CH3:37]>C1COCC1.O>[CH2:47]([O:46][CH:39]([O:38][CH2:36][CH3:37])/[C:40](/[O:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:14][CH:13]=1)=[CH:41]/[C:42]([O:44][CH3:45])=[O:43])[CH3:48]

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 157304-OctylphenolHCID 2855718-Crown-6HCID 10943174Methyl 4,4-diethoxybut-2-ynoate

Product 1

HCID 86748059HCID 86748059, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.06 g (10 mmol) of 4-octylphenol in 50 mL of THF was added 0.85 g (15 mmol) of powdered KOH and 3.98 g (15 mmol) of 18-crown-6. The solution was heated to 50° C. for 15 minutes, whereupon 2.8 g (15 mmol) of methyl 4,4-diethoxy-2-butynoate was added. The mixture was stirred for 30 minutes, then allowed to cool to room temperature. The solution was then poured into water, and extracted 3 times with 40 mL of ethyl acetate. The organic layers were combined, dried (MgSO4) and concentrated. The crude oil was subjected to column chromatography on SiO2. Elution with 20% ethyl acetate-hexane yielded 2.1 g (54%) of an oil, used in the next step without further purification.

Workup

  1. additionwas added
  2. extractionextracted 3 times with 40 mL of ethyl acetate
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. washElution with 20% ethyl acetate-hexane

Sources & evidence

ORD record
ord-4b9c6e3533a2421e84c69af987afb2a0
Source dataset
uspto-grants-1994_08
Patent number
US05336687

Reaction notes

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