Methanol → Methyl 6-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate

HRID 525468

Reaction equation

HRID 525468 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([C:12]([OH:14])=[O:13])[CH2:6][CH2:5]2.[CH3:15]O.S(=O)(=O)(O)O>>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([C:12]([O:14][CH3:15])=[O:13])[CH2:6][CH2:5]2

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 190700016-Hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

Product 1

HCID 58055117Methyl 6-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylateYield 100%

Procedure

To a solution of 6-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (0.5 g, 3 mmol) in methanol (6 mL, 200 mmol) was added sulfuric acid (0.05 g, 0.5 mmol) and stirred over weekend. After concentration, the residue was dissolved in EtOAc and washed with water, brine and dried over Na2SO4 to give the pure product as a white solid (0.55 g, 100%). LCMS: Rt=1.17 min, m/z=207.00 [M+], 100%.

Workup

  1. concentrationAfter concentration
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with water, brine
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-a7e6033a74cc4ee7948069f4f9150761
Source dataset
uspto-grants-2016_05
Patent number
US09340527B2

Linked notes

Loading…