Hydrochloric Acid → 2,3-Dimethyl-4-Phenyl-2,3-Butanediol

HRID 1706507Notes

Reaction equation

HRID 1706507 reaction equation
[OH:1][C:2]([CH3:7])([CH3:6])[C:3](=[O:5])[CH3:4].[CH2:8]([Mg]Cl)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl-].[NH4+].Cl>O1CCCC1>[CH3:6][C:2]([OH:1])([C:3]([CH3:4])([OH:5])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 82613-Hydroxy-3-methyl-2-butanoneHCID 25517Ammonium ChlorideHCID 178418336HCID 178418336, compound

Product 1

HCID 203361392,3-Dimethyl-4-Phenyl-2,3-Butanediol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 41 g. of 3-hydroxy-3-methyl-2-butanone in 300 ml. of dry tetrahydrofuran was treated at -10° under nitrogen with 500 ml. of 2M benzyl magnesium chloride and stirred at 25° C. for 20 hours. An aqueous ammonium chloride solution was added at 0° and the mixture was acidified at 0° with concentrated hydrochloric acid and extracted with ethyl acetate. The extract was evaporated and the residue chromatographed on silica gel. Elution with 20% ethyl acetate in hexane followed by recrystallization from the same solvent afforded 38 g. of the title product, m.p. 72°-74°, λmaxKBr 2.95, 3.35, 6.2, 6.63, 6.82, 7.23, 7.45, 7.65, 8.32, 8.70, 9.13, 10.58, 11.0, 11.40, 12.30, 12.97 and 14.06 μ.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe extract was evaporated
  3. customthe residue chromatographed on silica gel
  4. washElution with 20% ethyl acetate in hexane
  5. customfollowed by recrystallization from the same solvent
  6. customafforded 38 g

Sources & evidence

ORD record
ord-6e1cdf794f954cafa4bbf3ef9faf3a4d
Source dataset
uspto-grants-1980_06
Patent number
US04207419

Reaction notes

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