Sodium hydride → 1-(3-Cyclohexylmethoxy-5-methoxyphenyl)ethanone

HRID 657960Notes

Reaction equation

HRID 657960 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.Br[CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[H-].[Na+]>CN(C=O)C.CC(=O)OCC>[CH:15]1([CH2:14][O:1][C:2]2[CH:3]=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 137636Cyclohexane, (bromomethyl)-HCID 193506661-(3-Hydroxy-5-methoxyphenyl)ethanone

Product 1

HCID 581368141-(3-Cyclohexylmethoxy-5-methoxyphenyl)ethanoneYield 56.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

1-(3-Hydroxy-5-methoxyphenyl)ethanone (O3.033; 1.5 g) and bromomethylcyclohexane (1.76 g) were dissolved in DMF (20 ml), and sodium hydride (260 mg) was added. After stirring at 50° C. for 24 h, the DMF was drawn off. The residue was taken up in EA, washed with water, dried, filtered and concentrated. The residue was purified using silica gel (40 g cartridge, n-heptane/EA 0-50% within 30 min). 1.33 g of the title compound were obtained. LC-MS rt: 1.93 min [M+H]+: 263.2 (met. a)

Workup

  1. washwashed with water
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified
  6. customsilica gel (40 g cartridge, n-heptane/EA 0-50% within 30 min)

Sources & evidence

ORD record
ord-293d210696b045dd96371abb21bf1d1b
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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