Tetrahydrofuran → HCID 22452664, compound

HRID 2185904Notes

Reaction equation

HRID 2185904 reaction equation
[C:1]1([C:11]([O-:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-:14].[Na+].[CH2:16]1[CH2:20]OC[CH2:17]1>O>[CH:16]([O:14][C:3]1[CH:2]=[C:1]([C:11]([OH:13])=[O:12])[C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)([CH3:20])[CH3:17]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 50492651-Naphthoate

Product 1

HCID 22452664HCID 22452664, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of methyl 3-isopropoxy)-naphthalenecarboxylate (0.60 g, 2.46 mmol) in THF (30 mL), water (12 mL) and 1N NaOH (5.16 mL, 5.16 mmol) was stirred for 21 h at room temperature. The THF was removed in vacuo and the aqueous solution acidified to pH 1 with 1N HCl. The resulting precipitate was extracted with EtOAc, dried (MgSO4), filtered and concentrated to yield title acid as a white solid (0.53 g, 94% yield). 1H NMR (DMSO-d6) δ 13.22 (s, 1H), 8.71 (d, 1H), 7.90 (d, 1H), 7.68 (d, 1H), 7.60 (d, 1H), 7.47 (m, 2H), 4.81 (m, 1H), 1.36 (s, 3H), 1.34 (s, 3H). MS rm/z 229 (M−H).

Workup

  1. customThe THF was removed in vacuo
  2. extractionThe resulting precipitate was extracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c514183c232f401f97a23e99c017c6ef
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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