Acetone → HCID 20503926, compound

HRID 1725516Notes

Reaction equation

HRID 1725516 reaction equation
[C:1]([O:13]C)(=O)[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[CH3:15][C:16]([CH3:18])=[O:17].[H-].[Na+].Cl>C1(C)C=CC=CC=1.C(COC)OC.C1(C)C=CC=CC=1.O>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([C:1](=[O:13])[CH2:15][C:16](=[O:17])[CH3:18])=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 8441Dimethyl terephthalateHCID 24758Sodium hydride

Product 1

HCID 20503926HCID 20503926, compoundYield 25%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 69178531Toluene dimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of dimethyl terephthalate (10 g, 51.5 mmole) and acetone (4.15 mL, 56.6 mmole) in a mixture of toluene/dimethoxyethane (75 mL/25 mL) was added to a suspension of NaH 60% (2.68 g, 66.9 mmole) in dry toluene (25 mL) under argon. The mixture was heated at 100° C. for 4 hours. The reaction mixture was cooled to rt and 25 mL of water were added. The pH was adjusted to 3-4 with HCl 2N and the mixture was poured into water (300 mL). The aqueous mixture was extracted with ethyl acetate (3×150 mL), dried over sodium sulphate and evaporated to afford a yellow solid which was purified by column cromatography (n-Hex/EtOAc 9:1 to 7:3) to afford the title compound (2.78 g, 25% yield) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionThe aqueous mixture was extracted with ethyl acetate (3×150 mL)
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customto afford a yellow solid which
  6. customwas purified by column cromatography (n-Hex/EtOAc 9:1 to 7:3)

Sources & evidence

ORD record
ord-8307d21363054ee3bf07f9dbcb2d8110
Source dataset
uspto-grants-2009_02
Patent number
US07491722B2

Reaction notes

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