Formaldehyde → HCID 18980983, compound

HRID 482605Notes

Reaction equation

HRID 482605 reaction equation
[CH2:1]([O:4][CH:5]([CH3:15])[C:6]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)=[O:7])CC.[CH2:16]=[O:17].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.C(N([CH2:35][CH3:36])CC)C>N1C=CC=CC=1>[OH:17][CH2:16][C:5]([O:4][CH2:1][CH2:35][CH3:36])([CH3:15])[C:6]([C:8]1[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=1)=[O:7]

Participants

6

Reactant 4

HCID 712Formaldehyde2×HCID 8471TriethylamineHCID 66854Benzyltrimethylammonium hydroxideHCID 18980985HCID 18980985, compound

Product 1

HCID 18980983HCID 18980983, compoundYield 433.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 10 g (44 mmole) of 2-propoxy-4'-chloropropiophenone (Example 96c) in 10 g of pyridine was added 1.7 g (57 mmole) of paraformaldehyde and 0.4 g of a 40% methanolic solution of benzyltrimethylammonium hydroxide (Triton® B). After warming at 70° C. for two hours an additional 1.0 g of paraformaldehyde and 1.0 g of triethylamine was added. After heating for an additional two hours the mixture was partitioned between diethyl ether and dilute aqueous hydrochloric acid. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to yield 11 g of the crude title compound mixed with starting material.

Workup

  1. additionwas added
  2. temperatureAfter heating for an additional two hours the mixture
  3. customwas partitioned between diethyl ether and dilute aqueous hydrochloric acid
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c00ac3ba566a4a94b8d6fde60fa34cbf
Source dataset
uspto-grants-1998_08
Patent number
US05798311

Reaction notes

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