Hydrochloric Acid → HCID 13987404, compound

HRID 246803Notes

Reaction equation

HRID 246803 reaction equation
[OH:1][C:2]([CH3:14])([C:6]#[C:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O-:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].CO.Cl>O>[OH:1][C:2]([CH3:14])([C:6]#[C:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([OH:5])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11430Potassium CarbonateHCID 86741851HCID 86741851, compound

Product 1

HCID 13987404HCID 13987404, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A magnetically stirred mixture of 2.20 g (0.01 mole) of twice distilled 2-hydroxy-2-methyl-4-phenylbutynoate, ethyl ester 1.40 g (0.01 mole) of potassium carbonate and 3 ml of methanol in 20 ml of water was heated under a dry nitrogen atmosphere at 75°-80° C. for 1.5 hours, during which time the substrate dissolved to afford a faint yellow solution. After cooling, 20 ml of water was added and the solution was exhaustively extracted with ether. The aqueous phase was then treated with 1.5 g of Darco® activated carbon, filtered with suction through a Celite® pad and acidified in an ice bath with 2.0 ml (0.02 mole) of concentrated hydrochloric acid. The resulting oil was extracted with three 25 ml portions of ether and the combined extracts were washed with three 35 ml portions of water and dried over MgSO4. Filtration and concentration at the stripper provided an almost colorless oil which solidified on cooling. Recrystallization from hexane containing a trace of ether afforded 1.60 g (89% yield) of 2-hydroxy-2-methyl-4-phenylbutynoic acid as colorless plates, m.pt. 104.5°-106.0° C.

Workup

  1. temperaturewas heated under a dry nitrogen atmosphere at 75°-80° C. for 1.5 hours, during which time the substrate
  2. dissolutiondissolved
  3. customto afford a faint yellow solution
  4. temperatureAfter cooling
  5. extractionthe solution was exhaustively extracted with ether
  6. additionThe aqueous phase was then treated with 1.5 g of Darco® activated carbon
  7. filtrationfiltered with suction through a Celite® pad
  8. extractionThe resulting oil was extracted with three 25 ml portions of ether
  9. washthe combined extracts were washed with three 35 ml portions of water
  10. dry with materialdried over MgSO4
  11. filtrationFiltration and concentration at the stripper
  12. customprovided an almost colorless oil which
  13. temperatureon cooling
  14. customRecrystallization from hexane containing a trace of ether

Sources & evidence

ORD record
ord-664b3656252e4c0592a17ffc504e827e
Source dataset
uspto-grants-1987_11
Patent number
US04704161

Reaction notes

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