Hydrochloric Acid → [2,6-Di(propan-2-yl)phenyl]methanol

HRID 1756770Notes

Reaction equation

HRID 1756770 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]([C:10]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([CH3:21])[CH3:20])[C:11]=1[C:12](O)=[O:13])([CH3:9])[CH3:8].O.Cl>O1CCCC1.C(OCC)C>[CH:19]([C:15]1[CH:16]=[CH:17][CH:18]=[C:10]([CH:7]([CH3:9])[CH3:8])[C:11]=1[CH2:12][OH:13])([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 119589902,6-diisopropylbenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 45117178[2,6-Di(propan-2-yl)phenyl]methanolYield 39.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1.35 g (35.6 mmol) of lithium aluminum hydride in 60 ml of dry tetrahydrofuran was added 3.71 g (18 mmol) of 2, 6-diisopropylbenzoic acid, and the resultant mixture was refluxed with heating for 16 hours. After cooling, 80 ml of water was portionwise added to the mixture, which was mixed with 90 ml of ethyl ether. The mixture was strongly acidified with conc. hydrochloric acid. The aqueous layer was separated and shaken with ethyl ether. The organic layers were combined, washed with aqueous sodium hydroxide and then saturated saline, dried over anhydrous magnesium sulfate, and the solvent was evaporated in vacuo to give 1.37 g of 2, 6-diisopropylbenzyl alcohol as white solid.

Workup

  1. temperaturewith heating for 16 hours
  2. temperatureAfter cooling
  3. customThe aqueous layer was separated
  4. washwashed with aqueous sodium hydroxide
  5. dry with materialsaturated saline, dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-80912f2e88f048e1ae8a34a897e4f9ab
Source dataset
uspto-grants-1995_08
Patent number
US05442060

Reaction notes

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