Water → HCID 19068279, compound

HRID 1957709Notes

Reaction equation

HRID 1957709 reaction equation
[H-].[Na+].[C:3]12([C:13]3[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=3[OH:23])[C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.[CH3:24][O:25][CH2:26]Cl.O>CN(C=O)C>[C:3]12([C:13]3[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=3[O:23][CH2:24][O:25][CH3:26])[C:16]([O:18][CH3:19])=[O:17])[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 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 14852531HCID 14852531, compound

Product 1

HCID 19068279HCID 19068279, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

9 g (0.3 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 71.6 g (0.25 mol) of methyl 3-(1-adamantyl)-4-hydroxybenzoate in 500 ml of DMF was added dropwise and the mixture was stirred until the evolution of gas had ceased. 22.8 ml (0.3 mol) of methoxymethyl chloride were then added and the mixture was stirred at room temperature for one hour. The reaction medium was poured into water and extracted with ethyl ether. The organic phase was separated out after settling had taken place, dried over magnesium sulfate and evaporated. 67.7 g (82%) of the expected compound were recovered in the form of an oil.

Workup

  1. stirringthe mixture was stirred at room temperature for one hour
  2. extractionextracted with ethyl ether
  3. customThe organic phase was separated out
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. custom67.7 g (82%) of the expected compound were recovered in the form of an oil

Sources & evidence

ORD record
ord-7e6d6d0eaa8043d093c887d46981952b
Source dataset
uspto-grants-1998_07
Patent number
US05786379

Reaction notes

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