Hydrochloric Acid → 3-Methyl-(3-methylbenzyl)-butan-2-ol

HRID 985902Notes

Reaction equation

HRID 985902 reaction equation
C[Mg]Cl.C[C:5](C)([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=1)[CH:6]=[O:7].Cl.O1C[CH2:21][CH2:20][CH2:19]1>>[CH3:19][CH:20]([CH3:21])[CH:6]([OH:7])[CH2:5][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 13797308Benzenepropanal, alpha,alpha,3-trimethyl-HCID 178418332HCID 178418332, compound

Product 1

HCID 201586563-Methyl-(3-methylbenzyl)-butan-2-ol

Procedure

A solution of 10 g of methylmagnesium chloride in 100 ml of tetrahydrofuran was added at a temperature of from 25° C. to 30° C., and with the exclusion of air, to 17 g of 2,2-dimethyl-3-(3-methylphenyl)-propionaldehyde (according to Example 3). After 5 hours at 30° C., the reaction mixture was poured onto ice and acidified with hydrochloric acid. The phases were then separated and the organic phase was washed with 100 ml of water and 100 ml of sodium bicarbonate solution. Finally, drying was carried out with solid potassium carbonate. Fractional distillation yielded 15 g of end product at 0.12 mbar in a temperature range of from 79° C. to 82° C.

Workup

  1. additionthe reaction mixture was poured onto ice
  2. customThe phases were then separated
  3. washthe organic phase was washed with 100 ml of water and 100 ml of sodium bicarbonate solution
  4. customFinally, drying
  5. distillationFractional distillation
  6. customyielded 15 g of end product at 0.12 mbar in a temperature range of from 79° C. to 82° C.

Sources & evidence

ORD record
ord-51fdafb29f224aa58d96b9c3a0b52b9a
Source dataset
uspto-grants-1987_12
Patent number
US04710316

Reaction notes

Loading…