1-Bromohexane → 6-[4-(Hexyloxy)phenyl]-6-oxohexanoic acid

HRID 1720147Notes

Reaction equation

HRID 1720147 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[OH:8][C:9]1[CH:24]=[CH:23][C:12]([C:13]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21]C)=[O:20])=[O:14])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:2]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[O:14])=[CH:23][CH:24]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 22420384HCID 22420384, compound

Product 1

HCID 152955686-[4-(Hexyloxy)phenyl]-6-oxohexanoic acidYield 0.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The title compound is prepared from the methyl ester as follows. 1-Bromohexane (1.65 g, 10 moles) is heated under reflux for four hours with methyl 5-(4-hydroxybenzoyl)pentanoate (2 g, 8.5 moles) in a mixture of acetone (50 ml) and anhydrous potassium carbonate (2.35 g). The reaction mixture is filtered and evaporated under reduced pressure. The residue (3.3 g) is heated under reflux in 2N sodium hydroxide (26 ml) for four hours. The reaction mixture is partitioned between water (200 ml) and ether (300 ml). The ether phase is discarded and the aqueous phase is acidified to pH 1 with concentrated hydrochloric acid and extracted with ether (2×250 ml). The ether extract is dried over magnesium sulfate and evaporated under reduced pressure to a tan crystalline solid. Recrystallization from aqueous ethanol gives 5-(4-n-hexyloxybenzoyl)pentanoic acid (2.3 g) as colorless crystals, m.p. 95°-96° C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customevaporated under reduced pressure
  3. temperatureThe residue (3.3 g) is heated
  4. temperatureunder reflux in 2N sodium hydroxide (26 ml) for four hours
  5. customThe reaction mixture is partitioned between water (200 ml) and ether (300 ml)
  6. extractionextracted with ether (2×250 ml)
  7. extractionThe ether extract
  8. dry with materialis dried over magnesium sulfate
  9. customevaporated under reduced pressure to a tan crystalline solid
  10. customRecrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-971b744359764839ba29bfbf835a2d4b
Source dataset
uspto-grants-1996_04
Patent number
US05504244

Reaction notes

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