Hydrochloric Acid → HCID 21388144, compound

HRID 1833941Notes

Reaction equation

HRID 1833941 reaction equation
[CH3:1][C:2]([C:9]1[CH2:14][CH:13]=[C:12]([CH3:15])[CH2:11][CH:10]=1)([CH3:8])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].CC(C)([O-])C.[K+].Cl.[Cl-].[Na+]>CS(C)=O.C1(C)C=CC=CC=1>[CH3:8][C:2]([C:9]1[CH2:14][CH2:13][C:12]([CH3:15])=[CH:11][CH:10]=1)([CH3:1])[CH2:3][CH2:4][C:5]([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 21388142HCID 21388142, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21388144HCID 21388144, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolvent

Procedure

A mixture of 4 -methyl-4(4-methyl-1,4-cyclohexadien-1-yl)pentanoic acid (45.3 g, 0.22 mol), potassium t-butoxide (102 g, 0.91 mmol), toluene (110 ml) and dimethyl sulfoxide (1,000 ml) was stirred for 24 hours at room temperature. The solution was cooled, brought to neutral pH with hydrochloric acid, poured into 2 liters saturated sodium chloride, and extracted with methylene chloride. After the solution was washed with saturated sodium chloride solution and the solvent removed, the residual oil was distilled to yield 41.3 g (65.2%) of the 4-methyl-4(4-methyl-1,3-cyclohexadien-1-yl) pentanoic acid: bp 136°-138° (1 mm); nD20 1.5029; δmax 264 nm; δTMSCDCl3 11.15 (s,1), 5.62 (s,2), 2.06 (s,4) 1.78 (s,3), 1.05 (s,6).

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted with methylene chloride
  3. washAfter the solution was washed with saturated sodium chloride solution
  4. customthe solvent removed
  5. distillationthe residual oil was distilled

Sources & evidence

ORD record
ord-c016036b0f3343c38712fd95a332502b
Source dataset
uspto-grants-1978_01
Patent number
US04067906

Reaction notes

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