Water → 3-(1-Adamantyl)-1-bromo-4-methoxyethoxymethoxybenzene

HRID 482497

Reaction equation

HRID 482497 reaction equation
[H-].[Na+].[C:3]12([C:13]3[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=3[OH:20])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.[CH3:21][O:22][CH2:23][CH2:24][O:25][CH2:26]Cl.O>CN(C=O)C>[C:3]12([C:13]3[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=3[O:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26])[CH2:4][CH:5]3[CH2:11][CH:9]([CH2:8][CH:7]([CH2:6]3)[CH2:12]1)[CH2:10]2

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 46704942-(1-Adamantyl)-4-bromophenol

Product 1

HCID 153780873-(1-Adamantyl)-1-bromo-4-methoxyethoxymethoxybenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

3.8 g (0.13 mol) of sodium hydride (80% in oil) and 50 ml of DMF were introduced into a three-necked flask under a stream of nitrogen, a solution of 40 g (0.13 mol) of 2-(1-adamantyl)-4-bromophenol in 100 ml of DMF was then added dropwise and stirring was carried out until gas evolution has ceased. A solution of 18 ml (0.15 mol) of 2-methoxyethoxymethyl chloride in 20 ml of DMF was then added dropwise and stirring was carried out for four hours at room temperature. The reaction mixture was then poured into water and extracted with ethyl ether and the organic phase was separated by settling, washed with water, dried over magnesium sulphate and evaporated.

Workup

  1. stirringstirring
  2. extractionextracted with ethyl ether
  3. customthe organic phase was separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-459c0bec61064f74b8426f4edc3d0446
Source dataset
uspto-grants-1998_08
Patent number
US05798354

Linked notes

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