Hydrochloric Acid → HCID 13135244, compound

HRID 354539Notes

Reaction equation

HRID 354539 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[C:9]([CH3:19])=[C:10]([C:15]([CH3:18])=[CH:16][CH:17]=1)[C:11](OC)=[O:12].Cl>O1CCCC1.O>[Br:7][C:8]1[C:9]([CH3:19])=[C:10]([CH2:11][OH:12])[C:15]([CH3:18])=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 13135243methyl 3-bromo-2,6-dimethylbenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 13135244HCID 13135244, compoundYield 128.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent3×

Procedure

Using dried glassware, a solution of lithium aluminum hydride (0.79 gram, 0.021 mole) in dry tetrahydrofuran (90 ml) was cooled in a dry ice/acetone bath (78° C.) under a nitrogen atmosphere, and methyl 3-bromo-2,6-dimethylbenzoate (5.0 grams, 0.021 mole) in dry tetrahydrofuran (10 ml) was added. The mixture was stirred at room temperature for four hours, and a mixture of tetrahydrofuran (9 ml) in water (1 ml) was added, followed by water (10 ml) and 3 N hydrochloric acid until the solution was acidic. The reaction mixture was extracted with three 200 ml portions of diethyl ether. The combined extracts were dried over magnesium sulfate, filtered and the solvent evaporated to give (3-bromo-2,6-dimethylphenyl)methanol (5.8 grams). The ir spectrum was consistent with the named compound.

Workup

  1. customUsing dried glassware
  2. additionwas added
  3. extractionThe reaction mixture was extracted with three 200 ml portions of diethyl ether
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-4b3d63dd04714c8ebfd1076ecd6481da
Source dataset
uspto-grants-1983_03
Patent number
US04375476

Reaction notes

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