Sulfuric Acid → Methyl 2-(1-(3-hydroxyphenyl)cyclohexyl)acetate

HRID 1662588Notes

Reaction equation

HRID 1662588 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:14][C:15]([OH:17])=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.[C:23](=O)(O)[O-].[Na+]>CO>[OH:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:14][C:15]([O:17][CH3:23])=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 577064322-(1-(3-Hydroxyphenyl)cyclohexyl)acetic acid

Product 1

HCID 57705552Methyl 2-(1-(3-hydroxyphenyl)cyclohexyl)acetateYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude 2-(1-(3-hydroxyphenyl)cyclohexyl)acetic acid 105.C (1.01 g) was dissolved in MeOH (15 mL) and a catalytic (˜10 drops) amount of concentrated sulfuric acid was added. The mixture was then refluxed for 16 hours and then cooled to room temperature. The reaction was then made basic with saturated sodium bicarbonate solution and concentrated to dryness. The residue was then dissolved in EtOAc and water and the layers were separated. The aqueous layer was extracted (2×75 mL) with EtOAc. The combined organic layers were then washed with brine (1×75 mL) and dried over magnesium sulfate. The crude product was purified by medium pressure chromatography (silica, 0 to 15% EtOAc: DCM) to give methyl 2-(1-(3-hydroxyphenyl)cyclohexyl)acetate 105 (560 mg, 52% yield). MS ESI (pos.) m/e: 266.2 (M+H2O)+.

Workup

  1. temperatureThe mixture was then refluxed for 16 hours
  2. concentrationconcentrated to dryness
  3. dissolutionThe residue was then dissolved in EtOAc
  4. customwater and the layers were separated
  5. extractionThe aqueous layer was extracted (2×75 mL) with EtOAc
  6. washThe combined organic layers were then washed with brine (1×75 mL)
  7. dry with materialdried over magnesium sulfate
  8. customThe crude product was purified by medium pressure chromatography (silica, 0 to 15% EtOAc: DCM)

Sources & evidence

ORD record
ord-d30a330006cc40e39172eae152a96f72
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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