HCID 67958391, compound → HCID 67958030, compound

HRID 527631Notes

Reaction equation

HRID 527631 reaction equation
[OH:1][CH2:2][C:3]1[C:4]([CH2:10][C:11]([CH3:13])=[CH2:12])=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1>C(OCC)(=O)C.S(=O)(=O)(O)O.O>[CH3:12][C:11]1([CH3:13])[CH2:10][C:4]2[C:5]([OH:9])=[CH:6][CH:7]=[CH:8][C:3]=2[CH2:2][O:1]1

Participants

5

Reactant 1

HCID 67958391HCID 67958391, compound2×

Product 1

HCID 67958030HCID 67958030, compoundYield 36.5%

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

3-(hydroxymethyl)-2-(2-methylallyl)phenol (Intermediate 169, 360 mg, 2 mmol) was dissolved in ethyl acetate (20 ml), two drops of sulfuric acid were added to the solution that was stirred for 4 hours at room temperature. After this time the reaction was diluted with water (40 ml) and ethyl acetate (40 ml). Phases were separated and the organic layer was dried over Na2SO4 and evaporated in vacuo to afford a colourless oil. The oil was triturated with cyclohexane to obtain a white solid that was filtered, washed with cyclohexane (20 ml) and dried in vacuo to afford the title compound (130 mg).

Workup

  1. customPhases were separated
  2. dry with materialthe organic layer was dried over Na2SO4
  3. customevaporated in vacuo
  4. customto afford a colourless oil
  5. customThe oil was triturated with cyclohexane
  6. customto obtain a white solid
  7. filtrationthat was filtered
  8. washwashed with cyclohexane (20 ml)
  9. customdried in vacuo

Sources & evidence

ORD record
ord-a7e7001c9320474d9c3b6ea8a1b12920
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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