Hydrochloric Acid → HCID 23129000, compound

HRID 846567Notes

Reaction equation

HRID 846567 reaction equation
C(OOCC[CH2:7][C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=1)C.[CH3:15][CH:16]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:17](Cl)=[O:18].Cl.[O:27]1CCCC1>>[CH3:15][CH:16]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:17]([C:11]1[CH:12]=[CH:13][C:8]([CH2:7][OH:27])=[CH:9][CH:10]=1)=[O:18]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 128122322-Methyl octanoic acid chlorideHCID 86746052HCID 86746052, compound

Product 1

HCID 23129000HCID 23129000, compoundYield 14%

Conditions

Temperature
-78 °C

Procedure

To this solution was added dropwise 2.61 g (10.1 mmol) of the above 4-bromobenzyl-(1-ethoxy) ethyl ether over 40 minutes. After the completion of the addition, the mixture was heated under reflux for 1 hour and cooled to -78° C., to which was added dropwise 1.70 g (9.6 mmol) of (+)-2-methyl octanoic acid chloride dissolved in 20 ml of tetrahydrofuran over 40 minutes. The mixture was stirred at -78° C. for 3 hours and gradually turned to room temperature. It was added with 10 ml of a normal hydrochloric acid cooled at 0° C. and stirred for 1 hour. The product was extracted with ether and washed with a saturated aqueous solution of sodium hydrogen carbonate and further a saturated aqueous solution of sodium chloride. It was dried on anhydrous magnesium sulfate, and the oily matter after the removal of solvent was purified by a column chromatography of silica gel to obtain 323 mg (yield 14 %) of a colorless and oily 4-(2-methyloctanoyl) benzyl alcohol.

Workup

  1. additionAfter the completion of the addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 hour
  4. customgradually turned to room temperature
  5. temperaturecooled at 0° C.
  6. stirringstirred for 1 hour
  7. extractionThe product was extracted with ether
  8. washwashed with a saturated aqueous solution of sodium hydrogen carbonate
  9. dry with materialIt was dried on anhydrous magnesium sulfate
  10. customthe oily matter after the removal of solvent
  11. customwas purified by a column chromatography of silica gel

Sources & evidence

ORD record
ord-5079288a6dc343e69978e223f5f44fb4
Source dataset
uspto-grants-1992_08
Patent number
US05137653

Reaction notes

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