Water → HCID 20496709, compound

HRID 1074443Notes

Reaction equation

HRID 1074443 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](O)=[O:16])=[CH:6][CH:5]=1)([O-:3])=[O:2].O>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 962WaterHCID 204967086-(4-Nitrophenyl)hexanoic acid

Product 1

HCID 20496709HCID 20496709, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 9.1 g of 6-(4-nitrophenyl)hexanoic acid in 200 ml of dried tetrahydrofuran was added, dropwise, a solution of borane-dimethyl sulfide complex (0.042 mole) in 40 ml of dried tetrahydrofuran. The resulting mixture was stirred at room temperature for 16 hours and then heated at reflux for 1 hour before it was cooled again to room temperature. Water (10 ml) was added, the mixture was stirred for 15 minutes, most of the solvent was removed, and water was added to the residue. The resultant aqueous mixture was extracted with diethyl ether and the extract was washed with aqueous saturated sodium bicarbonate solution, water, and aqueous saturated sodium chloride solution and dried over magnesium sulfate. The solvent was then evaporated to leave 6-(4-nitrophenyl)hexanol as a yellow oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour before it
  3. temperaturewas cooled again to room temperature
  4. stirringthe mixture was stirred for 15 minutes, most of the solvent
  5. customwas removed
  6. additionwater was added to the residue
  7. extractionThe resultant aqueous mixture was extracted with diethyl ether
  8. washthe extract was washed with aqueous saturated sodium bicarbonate solution, water, and aqueous saturated sodium chloride solution
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-558e1882e01947e7a718a141a11336d6
Source dataset
uspto-grants-1983_07
Patent number
US04391818

Reaction notes

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