Citric Acid → 3-Methoxy-2-naphthoic acid

HRID 491058

反応式

HRID 491058 の反応式
[CH3:1][O:2][C:3]1[C:4]([C:13]([O:15]C)=[O:14])=[CH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.O.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[CH3:1][O:2][C:3]1[C:4]([C:13]([OH:15])=[O:14])=[CH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2

参加物

6

反応物 4

HCID 311Citric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 296952Methyl 3-Methoxy-2-naphthoate

生成物 1

HCID 701613-Methoxy-2-naphthoic acid収率 92%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of methyl 3-methoxy-2-naphthoate (6.28 g, 29.10 mmol) and water (10 mL) in MeOH (100 mL) at room temp. was treated with a 1 N NaOH solution (33.4 mL, 33.4 mmol). The mixture was heated at the reflux temp. for 3 h, cooled to room temp., and made acidic with a 10% citric acid solution. The resulting solution was extracted with EtOAc (2×100 mL). The combined organic layers were washed with a saturated NaCl solution, dried (MgSO4) and concentrated under reduced pressure. The residue was triturated with hexane then washed several times with hexane to give 3-methoxy-2-naphthoic acid as a white solid (5.40 g, 92%): 1H-NMR (DMSO-d6) δ 3.88 (s, 3H), 7.34-7.41 (m, 2H), 7.49-7.54 (m, 1H), 7.83 (d, J=8.09 Hz, 1H), 7.91 (d, J=8.09 Hz, 1H), 8.19 (s, 1H), 12.83 (brs, 1H).

後処理

  1. temperatureThe mixture was heated at the reflux temp
  2. temperaturecooled to room temp.
  3. extractionThe resulting solution was extracted with EtOAc (2×100 mL)
  4. washThe combined organic layers were washed with a saturated NaCl solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with hexane
  8. washthen washed several times with hexane

出典と根拠

ORDレコード
ord-55694919fbfa4e109130c9e51d2a8992
出典データセット
uspto-grants-2009_05
特許番号
US07528255B2

関連ノート

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