Water → 6-(Biphenyl-4-yl)hexanol

HRID 22438Notes

Reaction equation

HRID 22438 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[C:12]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][OH:2])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 54145223Methyl 6-([1,1'-biphenyl]-4-yl)hexanoate

Product 1

HCID 106586236-(Biphenyl-4-yl)hexanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

6-(Biphenyl-4-yl)hexanoic acid methyl ester (0.67 g, 2.4 mmol) in THF (5 ml) was added dropwise to lithium aluminium hydride (0.2 g, 5.3 mmol) in THF cooled to 0° C. After stirring for 1 day at room temperature, water (1 ml) then 5M sodium hydroxide (1 ml) followed by water (2 ml) were added cautiously followed by stirring at room temperature for 2 hours. The precipitate was filtered off and filtrate was evaporated to give 6-(biphenyl-4-yl)hexanol as a solid (MS: M+ =254).

Workup

  1. additionwere added cautiously
  2. stirringby stirring at room temperature for 2 hours
  3. filtrationThe precipitate was filtered off
  4. customfiltrate was evaporated

Sources & evidence

ORD record
ord-3469efc0c0bd4d1ea64b690e5edfb6e0
Source dataset
uspto-grants-1995_06
Patent number
US05428065

Reaction notes

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