Hydrochloric Acid → HCID 18950675, compound

HRID 1492538Notes

Reaction equation

HRID 1492538 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:20][O:21][CH2:22]Cl.Cl>C(Cl)Cl>[CH3:20][O:21][CH2:22][O:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7864Chloromethyl Methyl EtherHCID 265484-Hydroxybenzyl cyanideHCID 81531Diisopropylethylamine

Product 1

HCID 18950675HCID 18950675, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ten grams of 4-hydroxybenzyl cyanide was dissolved in 80 ml of methylene chloride, followed by addition of 20 ml of diisopropylethylamine and 9.1 g of chloromethyl methyl ether at 0 C., and stirred overnight at room temperature. The reaction solution was poured into 2N hydrogen chloride, followed by extraction of methylene chloride and washing in saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate to obtain residue. The residue was subjected to chromatography on a silica gel column, which was then eluted with chloroform to produce 12.8 g of 4-methoxymethyloxybenzyl cyanide.

Workup

  1. extractionfollowed by extraction of methylene chloride
  2. washwashing in saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customto obtain residue
  5. washwas then eluted with chloroform

Sources & evidence

ORD record
ord-0fe6eb1e73d74811baf24395a5e51d57
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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