Sodium Hydroxide → HCID 18442897, compound

HRID 458711Notes

Reaction equation

HRID 458711 reaction equation
[CH3:1][C:2]1([CH3:34])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([O:14][CH2:15][CH2:16][O:17][C:18]3[CH:33]=[CH:32][C:21]([CH2:22][CH:23]([C:28]([O:30]C)=[O:29])[C:24]([O:26]C)=[O:25])=[CH:20][CH:19]=3)[CH:5]=[CH:4][C:3]1=2.[OH-].[Na+]>CO.O1CCCC1>[CH3:1][C:2]1([CH3:34])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([O:14][CH2:15][CH2:16][O:17][C:18]3[CH:19]=[CH:20][C:21]([CH2:22][CH:23]([C:24]([OH:26])=[O:25])[C:28]([OH:30])=[O:29])=[CH:32][CH:33]=3)[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18442912HCID 18442912, compound

Product 1

HCID 18442897HCID 18442897, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl 4-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthoxy)ethoxy]benzylmalonate (1.50 g, 3.21 mmol) in a mixture of methanol (12.9 ml) and tetrahydrofuran (6.4 ml) is added a 2 mol/L aqueous solution of sodium hydroxide (8.01 ml, 16.03 mmol). The mixture is stirred for 2 hours at room temperature, and then the solvent was removed under a vacuum. The residue is dissolved in water and washed with ethyl acetate (10 ml). The aqueous solution is acidified to pH 2–3 with dilute hydrochloric acid and extracted with ethyl acetate (3×15 ml). The combined extracts are washed with water (20 ml) and brine (20 ml), dried over sodium sulfate, and concentrated. The residue is crystallized from ethyl acetate to give the title compound (1.38 g, 98%). HRMS calcd for C26H32O6: 440.5365. Found: 440.5363. MA calcd for C26H32O6: C, 70.89%; H, 7.32%. Found: C, 70.72%; H, 7.36%.

Workup

  1. customthe solvent was removed under a vacuum
  2. dissolutionThe residue is dissolved in water
  3. washwashed with ethyl acetate (10 ml)
  4. extractionextracted with ethyl acetate (3×15 ml)
  5. washThe combined extracts are washed with water (20 ml) and brine (20 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-ee027f5908ad495c8078e240f05b5c8c
Source dataset
uspto-grants-2007_03
Patent number
US07192970B2

Reaction notes

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