Methanol → Methyl 2-(7-hydroxynaphth-1-yl)ethanoate

HRID 429784Notes

Reaction equation

HRID 429784 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[CH2:12][C:13]([OH:15])=[O:14])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:20]O>>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[CH2:12][C:13]([O:15][CH3:20])=[O:14])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 18007940HCID 18007940, compound

Product 1

HCID 18007925Methyl 2-(7-hydroxynaphth-1-yl)ethanoate

Procedure

Dissolve the compound obtained in Step A in 100 ml of methanol. Cool the mixture in an ice-bath. Add thionyl chloride dropwise and maintain the reaction mixture at that temperature for 20 minutes after the addition. Leave for 1 hour at room temperature with stirring. Remove the methanol by evaporation under reduced pressure, and recrystallise the resulting solid from a mixture of toluene/cyclohexane (4/1).

Workup

  1. temperatureCool the mixture in an ice-bath
  2. additionafter the addition
  3. customLeave for 1 hour at room temperature
  4. customRemove the methanol
  5. customby evaporation under reduced pressure
  6. customrecrystallise the resulting solid
  7. additionfrom a mixture of toluene/cyclohexane (4/1)

Sources & evidence

ORD record
ord-45a15b665ca14d69b46df7eb85c8eabe
Source dataset
uspto-grants-2001_11
Patent number
US06319930B1

Reaction notes

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