4-Methoxybenzyl alcohol → HCID 19915369, compound

HRID 1090464Notes

Reaction equation

HRID 1090464 reaction equation
[H-].[Na+].COC1C=CC(CO)=CC=1.[H][H].[C:15]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH:32]([Br:37])[C:33](Br)([F:35])[F:34])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1.C(OCC)C>[C:15]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([Br:37])=[C:33]([F:35])[F:34])(=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 19915372HCID 19915372, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19915369HCID 19915369, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere a stirred mixture of 0.09 gram (0.0036 mole) of sodium hydride in 10 ml of tetrahydrofuran was cooled in an ice bath, and 0.5 gram (0.0036 mole) of 4-methoxyphenylmethanol was added dropwise. When the evolution of hydrogen ceased, a solution of 1.5 grams (0.0033 mole) of 9,10-dibromo-10,10-difluorodecyl benzoate in 5 ml of tetrahydrofuran was added dropwise. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature where it stirred for 18 hours. After this time the reaction mixture was taken up in 150 ml of diethyl ether and was washed with 50 ml of water and then with 50 ml of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The oil was subjected to column chromatography on silica gel. Elution was accomplished using methylene chloride. The appropriate fractions were combined and concentrated under reduced pressure yielding 0.44 gram of 9-bromo-10,10-difluoro-9-decenyl benzoate. The nmr spectrum was consistent with the proposed structure.

Workup

  1. temperaturewas cooled in an ice bath
  2. additionUpon completion of addition
  3. washwas washed with 50 ml of water
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
  7. washElution
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a583fef83a104f779d4fb4f2ba66be00
Source dataset
uspto-grants-1992_01
Patent number
US05081287

Reaction notes

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