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

HRID 5010Notes

Reaction equation

HRID 5010 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 1N 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 1N 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-f4c51992232e47eea151c3071a97aad7
Source dataset
uspto-grants-1993_09
Patent number
US05242936

Reaction notes

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