Hydrochloric Acid → 4-(4-Hydroxybutoxy)phenol

HRID 439767

Reaction equation

HRID 439767 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][CH2:8][CH2:9][C:10](OCC)=[O:11])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.Cl>CCOCC>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 189185904-(4-Hydroxy-phenoxy)-butyric acid ethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 224080554-(4-Hydroxybutoxy)phenol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 5.07 g of ethyl 4-(4-hydroxyphenoxy)butyrate in 23 ml of ether is added dropwise to a mixture of 1.72 g of lithium aluminum hydride in 90 ml of ether at a rate which maintains a gentle reflux. The mixture is stirred at ambient temperature for 6 hours, and then water is carefully added followed by 3N HCl to dissolve all solids. After separating the ether phase and extracting the aqueous phase twice with ether, the combined ether phases are washed with saturated NaHCO3, water, and brine and dried over MgSO4. Filtration and concentration yields 4-(4-hydroxyphenoxy) butan-1-ol as a white solid.

Workup

  1. dissolutionto dissolve all solids
  2. customAfter separating the ether phase
  3. extractionextracting the aqueous phase twice with ether
  4. washthe combined ether phases are washed with saturated NaHCO3, water, and brine
  5. dry with materialdried over MgSO4
  6. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-09e0d42b89f04892a1d4fddc6a5c8677
Source dataset
uspto-grants-1996_05
Patent number
US05516767

Linked notes

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