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Hydrochloric Acid → 2-Ethoxy-6-pentadecyl-benzyl alcohol

HRID 1768120
Notes
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Reaction equation

HRID 1768120 reaction equation
[CH2:1]([O:3][C:4]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:5]=1[C:6](OCC)=[O:7])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OC(=O)C)C.Cl>O1CCCC1.CCCCCC.CCOC(C)=O>[CH2:1]([O:3][C:4]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:5]=1[CH2:6][OH:7])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydride2×HCID 22574569Ethyl 2-Ethoxy-6-pentadecylbenzoate

Product 1

HCID 667019242-Ethoxy-6-pentadecyl-benzyl alcohol

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Ethyl 2-ethoxy-6-pentadecyl-benzoate (10.9 g, 27 mmol) was dissolved in dry tetrahydrofuran (60 mL). This solution was transferred to dry 250 mL three neck round bottom flask fitted with reflux condenser, mechanical stirrer and it was maintained under nitrogen atmosphere through out the reaction. To this lithium aluminum hydride (2.04 g, 54 mmol) was added slowly. Reaction was highly exothermic. After addition the solution was slowly brought to the reflux temperature and maintained at that temperature for about two hours and TLC was checked in hexane:EtOAc (8:2). After completion of reaction, excess lithium aluminum hydride was decomposed by drop-wise addition of ethylacetate (80 mL). To this 5 M HCl (100 mL) was added and organic layer was separated, dried over anhydrous sodium sulphate, concentrated under vacuum to give a light brownish solid. This was recrystallised from petroleum ether (40-60° C.) to give white solid. Yield: 8 g.

Workup

  1. dry with materialto dry 250 mL three neck round bottom flask
  2. customfitted
  3. temperaturewith reflux condenser, mechanical stirrer
  4. temperatureit was maintained under nitrogen atmosphere through out the reaction
  5. customReaction
  6. additionAfter addition the solution
  7. temperaturemaintained at that temperature for about two hours
  8. customorganic layer was separated
  9. dry with materialdried over anhydrous sodium sulphate
  10. concentrationconcentrated under vacuum
  11. customto give a light brownish solid
  12. customThis was recrystallised from petroleum ether (40-60° C.)
  13. customto give white solid

Sources & evidence

ORD record
ord-14017087944640269ad5bb83b0607ca8
Source dataset
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07235570B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes