Methyl 11-(p-tert-butylphenoxy)-undecanoate → 11-p-t-Butylphenoxy-1-undecanol

HRID 544596Notes

Reaction equation

HRID 544596 reaction equation
[C:1]([C:5]1[CH:25]=[CH:24][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](OC)=[O:21])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[C:1]([C:5]1[CH:25]=[CH:24][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 19797514Methyl 11-(p-tert-butylphenoxy)-undecanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 1331374011-p-t-Butylphenoxy-1-undecanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The methyl 11-(p-tert-butylphenoxy)-undecanoate, 3.7 g, 10.6 mmoles, was dissolved in 100 ml dry diethyl ether and added, dropwise, to a stirred slurry of 0.5 g lithium aluminum hydride in 100 ml dry diethyl ether. After one hour the reaction mixture was filtered through Celite and the filtrate was treated with 100 ml 1 N hydrochloric acid. The organic layer was removed, dried (MgSO4), and concentrated to a yellow oil, 2.7 g. The oil was chromatographed on 200 g 90 to 200 mesh silica gel (2% MeOH/CH2Cl2 eluent) collecting the product as a white, waxy solid. The solid was recrystallized from warm pentane yielding pure 11-(p-tert-butylphenoxy)-undecanol, 1.1 g, m.p. 39° to 40° C.

Workup

  1. additionadded
  2. filtrationAfter one hour the reaction mixture was filtered through Celite
  3. additionthe filtrate was treated with 100 ml 1 N hydrochloric acid
  4. customThe organic layer was removed
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to a yellow oil, 2.7 g
  7. customThe oil was chromatographed on 200 g 90 to 200 mesh silica gel (2% MeOH/CH2Cl2 eluent)
  8. customcollecting the product as a white, waxy solid
  9. customThe solid was recrystallized
  10. temperaturefrom warm pentane yielding pure 11-(p-tert-butylphenoxy)-undecanol, 1.1 g, m.p. 39° to 40° C.

Sources & evidence

ORD record
ord-667b857935554005b88bdb8daf9b0b70
Source dataset
uspto-grants-1984_05
Patent number
US04451474

Reaction notes

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