Sodium hydride → HCID 54149611, compound

HRID 1110088Notes

Reaction equation

HRID 1110088 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[CH2:9][CH2:10][CH3:11].[H-].[Na+].[C:14]([C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20]Br)([O:16][CH3:17])=[O:15].CCCCCC.C(OCC)(=O)C>CN(C)C=O.C(OCC)(=O)C>[CH3:17][O:16][C:14](=[O:15])[C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[CH2:9][CH2:10][CH3:11]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 2620601,3-Benzenediol, propyl-HCID 2734813Methyl 2-(bromomethyl)benzoateHCID 21226206Ethyl acetate hexane

Product 1

HCID 54149611HCID 54149611, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1,3-dihydroxy-2-propylbenzene (5.00 g, 33.3 mmol) in dimethylformamide (10 mL) was treated with 97% sodium hydride (880 mg, 36.6 mmol ) as room temperature for 20 minutes. 2-(Carbomethoxy)benzyl bromide (7.62 g, 33.3 mmol) was added in one portion and the resulting mixture stirred at room temperature for 24 hours. The mixture was diluted with ethyl acetate and washed once with brine. The organic layer was dried (sodium sulfate), filtered, and concentrated in vacuo to provide a brown oil. Silica gel chromatography (hexane/ethyl acetate) provided 2.10 g (21%) of the title intermediate as a colorless oil: 1H--NMR (CDCl3), 8.08 (d, J=8 Hz, 1H), 7.84 (d, J=8 Hz, 1H), 7.61 (t, J=8 Hz, 1H), 7.41 (t, J=8 Hz, 1H), 7.02 (t, J=8 Hz, 1H), 6.58 (d, J=8 Hz, 1H), 6.50 (d, J=8 Hz, 1H), 5.52 (s, 2H), 5.16 (s, 1H, --OH), 3.94 (s, 3H), 2.78 (t, J=7 Hz, 2H), 1.67 (hextet, J=8 Hz, 2H), 1.03 (t, J=8 Hz, 3H).

Workup

  1. washwashed once with brine
  2. dry with materialThe organic layer was dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto provide a brown oil

Sources & evidence

ORD record
ord-81d0b16c16e249889e5b9958e809e1a9
Source dataset
uspto-grants-1994_06
Patent number
US05324743

Reaction notes

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