Hydrochloric Acid → [2,6-Dimethyl-3-(1-methylethyl)phenyl]methanol

HRID 354545Notes

Reaction equation

HRID 354545 reaction equation
[CH3:1][C:2]1[C:12]([CH:13]([CH3:15])[CH3:14])=[CH:11][CH:10]=[C:9]([CH3:16])[C:3]=1[C:4](OCC)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>COCCOC.O>[CH3:1][C:2]1[C:12]([CH:13]([CH3:15])[CH3:14])=[CH:11][CH:10]=[C:9]([CH3:16])[C:3]=1[CH2:4][OH:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 13126300Ethyl 2,6-dimethyl-3-(propan-2-yl)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 20437159[2,6-Dimethyl-3-(1-methylethyl)phenyl]methanolYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

A solution of ethyl 2,6-dimethyl-3-(1-methylethyl)benzoate (2.8 g) in dry 1,2-dimethoxyethane (40 ml) was added dropwise under a nitrogen atmosphere to a stirred solution of lithium aluminum hydride in dry 1,2-dimethoxyethane (80 ml) at approximately -78°. The mixture was allowed to warm to ambient temperature. The mixture was heated to reflux and maintained under reflux for one hour. After cooling to ambient temperature, a solution of 1,2-dimethoxyethane (20 ml) in water (5 ml) was added dropwise to the reaction mixture, followed by additional water (25 ml). The reaction mixture was acidified with 3 N hydrochloric acid and extracted with diethyl ether. The combined ether extracts were dried over magnesium sulfate, filtered, and the solvent evaporated to give [2,6-dimethyl-3-(1-methylethyl)phenyl]methanol (1.7 g). The nmr spectrum was consistent with the proposed structure.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperaturemaintained
  4. temperatureunder reflux for one hour
  5. temperatureAfter cooling to ambient temperature
  6. extractionextracted with diethyl ether
  7. dry with materialThe combined ether extracts were dried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent evaporated

Sources & evidence

ORD record
ord-b62fae0c98e64af3a07e9cad7e5a67ce
Source dataset
uspto-grants-1983_03
Patent number
US04375476

Reaction notes

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