Water → 4-(1,3-Diphenyl-1-propoxy)benzyl alcohol

HRID 363016Notes

Reaction equation

HRID 363016 reaction equation
[C:1]1([CH:7]([O:16][C:17]2[CH:27]=[CH:26][C:20]([C:21](OCC)=[O:22])=[CH:19][CH:18]=2)[CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[C:1]1([CH:7]([O:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:21][OH:22])=[CH:26][CH:27]=2)[CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 54012855Ethyl 4-(1,3-diphenyl-1-propoxy)benzoate

Product 1

HCID 541185434-(1,3-Diphenyl-1-propoxy)benzyl alcohol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 6-4 (2.46 g, 6.8 mmol) in ether (30 ml) was added dropwise under nitrogen atmosphere to a stirred cold suspension of lithium aluminum hydride (0.285 g, 7.5 mmol) in ether (5 ml). The mixture was stirred for 3 hrs at ambient temperature and was decomposed by carefully adding water and sodium hydroxide. This mixture was extracted with ethyl acetate. The extract was washed with water, dried, filtered and concentrated in vacuo to yield 6-5 as a colorless viscious oil.

Workup

  1. extractionThis mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4bdf7a1b29cc4431b4e9bab4438c3aaa
Source dataset
uspto-grants-1999_02
Patent number
US05872138

Reaction notes

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