Formaldehyde → HCID 13824274, compound

HRID 1906874Notes

Reaction equation

HRID 1906874 reaction equation
[C:1]([C:6]1[C:7]([Cl:19])=[C:8]([Cl:18])[C:9]2[O:13][CH:12]([C:14]([OH:16])=[O:15])[CH2:11][C:10]=2[CH:17]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].Cl.[CH3:21]NC.C=O>C(O)(=O)C.CN(C)C=O>[Cl:19][C:7]1[C:6]([C:1](=[O:5])[C:2](=[CH2:21])[CH2:3][CH3:4])=[CH:17][C:10]2[CH2:11][CH:12]([C:14]([OH:16])=[O:15])[O:13][C:9]=2[C:8]=1[Cl:18]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 13824273HCID 13824273, compound

Product 1

HCID 13824274HCID 13824274, compoundYield 71.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 5-butyryl-6,7-dichloro-2,3-dihydro-2-benzofurancarboxylic acid (12.0 g, 0.04 mole), dimethylamine hydrochloride (4.3 g, 0.052 mole), para-formaldehyde (1.9 g, 0.063 mole) and acetic acid (4 drops) was heated on a steam bath for 21/2 hours. Dimethylformamide (35 ml) was added and heating was continued for 11/2 hours. The reaction mixture was poured into ice water, extracted with ether, washed with water and dried over magnesium sulfate. The ether was evaporated in vacuo and the residue triturated with butyl chloride (100 ml) to give 9.0 g of 6,7-dichloro-2,3-dihydro-5-(2-methylenebutyryl)-2-benzofurancarboxylic acid which melted at 148° C.

Workup

  1. temperaturewas heated on a steam bath for 21/2 hours
  2. temperatureheating
  3. custom2 hours
  4. extractionextracted with ether
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customThe ether was evaporated in vacuo
  8. customthe residue triturated with butyl chloride (100 ml)

Sources & evidence

ORD record
ord-c4d33a16bd5b45118666c75a055336ff
Source dataset
uspto-grants-1987_03
Patent number
US04654365

Reaction notes

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