Hydrochloric Acid → (+/-)-3-(2,4-Dihydroxyphenyl)-1-methylcyclohexanol

HRID 585699Notes

Reaction equation

HRID 585699 reaction equation
[CH3:1][Mg]Cl.[OH:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[CH:12]1[CH2:17][CH2:16][CH2:15][C:14](=[O:18])[CH2:13]1.Cl>O1CCCC1>[OH:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[CH:12]1[CH2:17][CH2:16][CH2:15][C:14]([CH3:1])([OH:18])[CH2:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12788196(+/-)-3-(2,4-Dihydroxyphenyl)cyclohexanoneHCID 178418332HCID 178418332, compound

Product 1

HCID 22337786(+/-)-3-(2,4-Dihydroxyphenyl)-1-methylcyclohexanolYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl magnesium chloride (0.132 ml of a 22% w/w solution in tetrahydrofuran) was added to a solution of (±)-3-(2,4-dihydroxyphenyl)cyclohexanone (20 mg) in tetrahydrofuran (3 ml) at 0° C. under argon. After 16 hr, dilute hydrochloric acid (1 ml) was added dropwise and the reaction mixture was partitioned between ethyl acetate (50 ml) and brine (50 ml). The aqueous layer was extracted with ethyl acetate (2×50 ml), and the combined organic extracts were dried over magnesium sulfate and evaporated in vacuo. The crude residue was purified by preparative HPLC to furnish the title compound as a white solid (6 mg, 28%). δH (d4-MeOH) 1.20 (3H, s), 1.22-1.39 (2H, overlapping m), 1.46 (1H, t), 1.54-1.87 (5H, overlapping m), 3.22 (1H, m), 6.19-6.25 (2H, overlapping m), 6.86 91H, d); m/z (ES−) 281 (M+60−H)−.

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate (50 ml) and brine (50 ml)
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×50 ml)
  3. dry with materialthe combined organic extracts were dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe crude residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-9edc428806434618b2dab1a0861467a1
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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