Hydrochloric Acid → HCID 15295569, compound

HRID 1720148Notes

Reaction equation

HRID 1720148 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:5].[CH2:17](Br)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[OH-].[K+].Cl>O>[CH2:17]([O:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:5])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81011-BromohexaneHCID 14797Potassium HydroxideHCID 14844815HCID 14844815, compound

Product 1

HCID 15295569HCID 15295569, compoundYield 0%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-(2-hydroxybenzoyl)pentanoic acid (1.5 g, 6.75 moles), hexyl bromide (1.28 g, 7.75 moles), potassium hydroxide (1.3 g) and water (7 ml) is heated under reflux (5 hours). The reaction mixture is neutralized with hydrochloride acid and extracted with ether (3×30 ml). The ether extract is dried over magnesium sulfate, filtered and evaporated. The residue is chromatographed on a silica gel column (hexane:ether: acetic acid; 74:25:1) to provide a crude product which on recrystallization from heptane gives 5-(2-n-hexyloxybenzoyl) pentanoic acid (1.0 g) as a white crystalline solid, m.p. 64°-65° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux (5 hours)
  3. extractionextracted with ether (3×30 ml)
  4. extractionThe ether extract
  5. dry with materialis dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is chromatographed on a silica gel column (hexane:ether: acetic acid; 74:25:1)
  9. customto provide a crude product which
  10. customon recrystallization from heptane

Sources & evidence

ORD record
ord-ddc101bcacc24ae7a2af462d11a73fdf
Source dataset
uspto-grants-1996_04
Patent number
US05504244

Reaction notes

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