1-Butanol → N,N-Dimethylaniline

HRID 1248477Notes

Reaction equation

HRID 1248477 reaction equation
S(=O)(=O)(O)[OH:2].[CH3:6][N:7]([CH3:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:15]([OH:19])CCC.CC[O:22][CH2:23][CH3:24].[CH3:25][OH:26]>>[CH3:6][N:7]([CH3:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:24]1([OH:2])[C:15](=[O:19])[C:25](=[O:26])[C:23]=1[OH:22]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 949N,N-DimethylanilineHCID 1118Sulfuric AcidHCID 21864698Diethyl ether methanol

Product 2

HCID 949N,N-DimethylanilineHCID 17913Squaric acid

Conditions

Temperature
126 °C

Procedure

Methyl squarate 0.64 grams, 5 millimoles, prepared as described in the Journal American Chemical Society, Vol. 88, pp. 1533-1536 (1966) was placed in a 100 milliliter 3-neck flask containing 0.1 milliliters of concentrated sulfuric acid, 1.23 grams, 10.2 millimoles of N,N-dimethylaniline, and 10 milliliters of dry 1-butanol (dried over 3 Angstrom molecular sieves). The above mixture was brought to reflux at an oil bath temperature of about 126° C. under a nitrogen atmosphere. After 24 hours, the mixture was cooled to room temperature, and 2 milliliters triethylanime, 30 milliliters ether/methanol (1:1) were added to the solution mixture. The precipitated product, bis(4-dimethylaminophenyl)squaraine was separated by filtration with a medium sintered glass funnel, followed by washing with an ether/methanol (1:1) solution, this washing continuing until the filtrate is light blue. After vacuum drying, there resulted 0.59 grams (37 percent), of bis(4-dimethylaminophenyl)squaraine as identified by a comparison of its properties, including melting point, and infrared (IR) spectrum with identical data generated for the squaraine obtained from the reaction of N,N-dimethylaniline and squaric acid.

Workup

  1. customMethyl squarate 0.64 grams, 5 millimoles, prepared
  2. custom1533-1536 (1966) was placed in a 100 milliliter 3-neck flask
  3. temperaturethe mixture was cooled to room temperature
  4. customThe precipitated product, bis(4-dimethylaminophenyl)squaraine was separated by filtration with a medium sintered glass funnel
  5. washby washing with an ether/methanol (1:1) solution
  6. customAfter vacuum drying
  7. customthere resulted 0.59 grams (37 percent)

Sources & evidence

ORD record
ord-0dc0f97e34514ffdac5fbe883aada8a8
Source dataset
uspto-grants-1985_06
Patent number
US04524219

Reaction notes

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