Synthesis of 3-diethylaminophenol (N,N-diethyl-3-aminophenol)

Preparation of 3-diethylaminophenol

Preparation of 3-diethylaminophenol (N,N-Diethyl-3-aminophenol)

Preparation of 3-diethylaminophenol (N,N-Diethyl-3-aminophenol)

150 g of oleum containing 30 % sulfur trioxide are placed in a 500 ml round bottom flask fitted with a reflux condenser and heated to 100° C. The diethylaniline is added drop by drop during half an hour. The heating is continued till a sample, rendered alkaline and extracted with ether, gives no residue of diethylaniline after evaporation of the ether. The product is then allowed to cool, poured into 1 liter of water, and nearly neutralized with calcium oxide. The calcium sulfate is filtered off’ washed well, and sodium carbonate added to the filtrate till no further precipitate is produced. The precipitate is filtered, and the solution of the sodium salt of diethylaniline metasulfonic acid evaporated to dryness. The sodium salt of the diethylaniline metasulfonic acid is converted into the 3-diethylaminophenol by fusion with sodium hydroxide. The fusion is done in a nickel crucible of 250 ml capacity, which is heated in an oil-bath. One part of the dry sodium salt of the diethylaniline metasulfonic acid is added gradually to a mixture of one part of sodium hydroxide and one-third of a part of water, which is heated to 260-270° C. During the addition of the sodium salt the contents of the crucible are well stirred by a thermometer encased in a copper tube. When all the sodium salt of the diethylaniline metasulfonic acid has been added the temperature is maintained at 270° for five minutes and the mass allowed to cool. The contents of the crucible are, when cold, extracted several times with water acidified with hydrochloric acid, and the neutralized solution evaporated to a small bulk, when the 3-diethylaminophenol crystallizes out. This is filtered and dried yielding 3-diethylaminophenol with melting point 14°C, boiling point 275-280° C.

The Synthetic Dyestuffs and the Intermediate Products from which They are Derived, by J. C. Cain, 205-206, 1905

IUPAC Name

3-(diethylamino)phenol

InChI

InChI=1S/C10H15NO/c1-3-11(4-2)9-6-5-7-10(12)8-9/h5-8,12H,3-4H2,1-2H3

InChI Key

WAVOOWVINKGEHS-UHFFFAOYSA-N

Canonical SMILES

CCN(CC)C1=CC(=CC=C1)O

Depositor-Supplied Synonyms

3-(Diethylamino)phenol, 3-DIETHYLAMINOPHENOL, 91-68-9, Phenol, 3-(diethylamino)-, N,N-Diethyl-3-aminophenol, m-(Diethylamino)phenol, N,N-Diethyl-m-aminophenol, Phenol, m-(diethylamino)-, 3-Hydroxy-N,N-diethylaniline, N,N-Diethyl-3-hydroxyaniline, 3-(Diethylamino) Phenol, NSC 93934, CCRIS 4615, WAVOOWVINKGEHS-UHFFFAOYSA-N, EINECS 202-090-9, BRN 0908212, AI3-14895, ST50406246, NSC93934, 3-diethylamino phenol, 3-diethylamino-phenol, PubChem19876, 3-n,n-diethylaminophenol, AC1Q2YYT, AC1Q7AKA, DSSTox_CID_5037, ACMC-209rd0, UNII-BQY98Q7YU5, AC1L1NX4, AC1Q2Z5J, BQY98Q7YU5, DSSTox_RID_77634, 3-(N,N-diethylamino)phenol, DSSTox_GSID_25037, KSC490K5L, BIDD:GT0214, SCHEMBL124477, 102091_ALDRICH, CHEMBL1420719, 31880_FLUKA, CTK3J0555, MolPort-001-792-009, Tox21_200238, ANW-39730, AR-1E7525, NSC-93934, STL264114, AKOS000118745, LS-1928, MCULE-3925632697, NE10161, RP22832, RTR-028890, CAS-91-68-9, NCGC00091617-01, NCGC00091617-02, NCGC00257792-01, AJ-20396, AK-76050, AN-42574, L527, AB1011782, DB-021710, KB-178493, KB-183728, ST2404806, TR-028890, D0470, FT-0688169, 4-13-00-00969 (Beilstein Handbook Reference), I01-9734, 3B3-032662, N,N-Diethyl-3-aminophenol; Phenol,3-(diethylamino)-(9CI)

Removed Synonyms

CID7062, 97-61-0

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2 comments

  1. Dr.Sisir

    It’s a very interesting and commendable effort of yours to create and maintain this site . It’s almost 12 years now since I am retired from active process and product development in an wide area of fine chemicals both organic and inorganic including bulk actives and intermediates. Certainly it would be pleasure for me to share the wide experience and expertise in chemical synthesis both small and large scale production. I have a good credential and would help in an unstinted way , particularly those companies in Vietnam, Srilanka, Thailand ,Cambodia .
    Thanks to your efforts
    Dr.S.K.Adhikari
    Bombay

  2. Dr.Sisir

    It’s a very interesting and commendable effort. It’s now almost retired from active process and product development in an wide area of fine chemicals both organic and inorganic including bulk actives and intermediates. Certainly it would be pleasure to share the wide experience and expertise in chemical synthesis. I have a good credential and would help particularly those companies in Vietnam, Srilanka, Thailand ,Cambodia .
    Thanks to your efforts
    Dr.S.K.Adhikari
    Bombay

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