Sodium Hydroxide → HCID 59441459, compound

HRID 391161Notes

Reaction equation

HRID 391161 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([O:13]C(=O)C)[CH2:7]2)(=[O:3])[CH3:2].[OH-].[Na+]>O1CCOCC1.O>[OH:13][CH:8]1[CH2:7][C:6]2[C:10](=[CH:11][CH:12]=[C:4]([C:1](=[O:3])[CH3:2])[CH:5]=2)[CH2:9]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 189215235-Acetyl-2,3-dihydro-1H-inden-2-yl acetate

Product 1

HCID 59441459HCID 59441459, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of acetic acid 5-acetyl-indan-2-yl ester (Compound E-24; 1.50 g, 6.87 mmol) in dioxane (7 mL) was treated with 1.0 N sodium hydroxide (NaOH; 7.7 mL), and the solution was stirred at room temperature overnight. The solution was diluted with H2O (25 mL) and was extracted with CH2Cl2 (2×). The combined extracts were dried (MgSO4) and concentrated to give the title compound (1.06 g, 88%): 1H NMR δ 7.85 (s, 1H), 7.79 (m, 1H), 7.33 (d, J=7.7 Hz, 1H), 4.76 (m, 1H), 3.29-3.21 (m, 2H), 3.00-2.94 (m, 2H), 2.59 (s, 3H), 1.73 (d, J=5.3 Hz, 1H); ELMS m/z 176 (M+, 76), 161 (100).

Workup

  1. extractionwas extracted with CH2Cl2 (2×)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-07b05e23000948b183eae89bb2378a89
Source dataset
uspto-grants-2013_02
Patent number
US08383786B2

Reaction notes

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