Borane → 6-Phenyl-1-hexanol

HRID 1703103Notes

Reaction equation

HRID 1703103 reaction equation
B.[C:2]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](O)=[O:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1>[C:2]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6331Borane2×HCID 796956-Phenylhexanoic Acid

Product 1

HCID 5201106-Phenyl-1-hexanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 100 ml. of 1 molar borane in tetrahydrofuran cooled in an ice bath is added 19.2 g. of 6-phenylhexanoic acid over a period of 30 minutes. The solution is stirred for 1.5 hours and an additional 100 ml. of 1 molar borane in tetrahydrofuran is added. After stirring overnight at room temperature the reaction mixture is poured into 500 g. of ice. The mixture is extracted with ether, the extracts washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give 6-phenylhexanol as a light yellow liquid.

Workup

  1. additionis added 19.2 g
  2. stirringAfter stirring overnight at room temperature the reaction mixture
  3. additionis poured into 500 g
  4. extractionThe mixture is extracted with ether
  5. washthe extracts washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-57103ceed045404c9c49d0560191cbce
Source dataset
uspto-grants-1982_09
Patent number
US04350822

Reaction notes

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