Hydrochloric Acid → 6-(4-Acetyl-3-hydroxy-2-propylphenoxy)-2,2-dimethylhexanoic acid

HRID 543224Notes

Reaction equation

HRID 543224 reaction equation
[C:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([CH3:19])([CH3:18])[C:14]([O:16]C)=[O:15])=[C:6]([CH2:22][CH2:23][CH3:24])[C:5]=1[OH:25])(=[O:3])[CH3:2].[I-].[Li+].N1C(C)=CC(C)=CC=1C.Cl>>[C:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([CH3:19])([CH3:18])[C:14]([OH:16])=[O:15])=[C:6]([CH2:22][CH2:23][CH3:24])[C:5]=1[OH:25])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 79532,4,6-TrimethylpyridineHCID 66321Lithium iodideHCID 21294040Methyl 6-(4-acetyl-3-hydroxy-2-propylphenoxy)-2,2-dimethylhexanoate

Product 1

HCID 138819776-(4-Acetyl-3-hydroxy-2-propylphenoxy)-2,2-dimethylhexanoic acid

Procedure

A solution of 1.1 g. of methyl 6-(4-acetyl-3-hydroxy-2-propylphenoxy)-2,2-dimethylhexanoate and 2.6 g. of lithium iodide in 50 ml. of collidine was heated to 100° C. under a nitrogen blanket for about 46 hours. The reaction mixture was then added to ice. After making the solution acidic with hydrochloric acid, the solution was extracted with ether. The ether phase was washed three times with a 10% sodium bicarbonate solution. The ether solution was then further washed with a dilute hydrochloric acid solution, water, and a saturated sodium chloride solution. Evaporating the ether layer to dryness gave 1.03 g. of the title product, M+ =336; NMR.

Workup

  1. additionThe reaction mixture was then added to ice
  2. extractionthe solution was extracted with ether
  3. washThe ether phase was washed three times with a 10% sodium bicarbonate solution
  4. washThe ether solution was then further washed with a dilute hydrochloric acid solution, water
  5. customEvaporating the ether layer to dryness
  6. customgave 1.03 g

Sources & evidence

ORD record
ord-c5bc63499a1c4526b574e96e95508072
Source dataset
uspto-grants-1987_04
Patent number
US04661505

Reaction notes

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