Synthesis of 3-acetamidophenol

Preparation of 3-acetamidophenol

Preparation of 3-acetamidophenol

Preparation of 3-acetamidophenol

Acetylation reaction is carried out by dissolving m-aminophenol in the minimum amount of warm 50 % acetic acid. The the solution is cooled to room temperature, and 1.1 molecular equivalents of acetic anhydride is added. The reaction mixture is stirred for one-half hour and  the solution is diluted with an equal volume of ice-cold distilled water and chilled yielding solid product (sometimes rubbing the walls of the vessel is necessary to complete the crystallization process). The acetylated product is filtered off, washed with ice water, and dried. 3-Acetamidophenol melts at 148-149° C and is sufficiently pure for preparative purposes.

An advanced laboratory manual of organic chemistry, M. Heidelberger, 34, 1923

IUPAC Name

N-(3-hydroxyphenyl)acetamide

InChI

InChI=1S/C8H9NO2/c1-6(10)9-7-3-2-4-8(11)5-7/h2-5,11H,1H3,(H,9,10)

InChI Key

QLNWXBAGRTUKKI-UHFFFAOYSA-N

Canonical SMILES

CC(=O)NC1=CC(=CC=C1)O

MeSH Synonyms

3-hydroxyacetanilide, acetyl-2-aminophenol, acetyl-m-aminophenol

Depositor-Supplied Synonyms

3-Acetamidophenol, N-(3-Hydroxyphenyl)acetamide, 3′-Hydroxyacetanilide, Metacetamol, 621-42-1, m-Acetamidophenol, 3-Hydroxyacetanilide, N-Acetyl-m-aminophenol, M-HYDROXYACETANILIDE, 3-(Acetylamino)phenol, Pedituss, Metalid, Pyrapap, Rystal, m-(Acetylamino)phenol, m-Acetaminophenol, Acetamide, N-(3-hydroxyphenyl)-, Acetanilide, 3′-hydroxy-, 3-(Acetylamino)-1-hydroxybenzene, Metacetamolum, BS 749, Metacetamolo [DCIT], 3-ACETAMINOPHENOL, NSC 3990, Metacetamolum [INN-Latin], ACETAMIDOPHENOL(3-), UNII-V942ZCN81H, CCRIS 4567, CHEBI:76987, QLNWXBAGRTUKKI-UHFFFAOYSA-N, EINECS 210-687-0, BS 479, BRN 0907998, NCGC00091423-02, AI3-01929, DSSTox_CID_2089, DSSTox_RID_76484, DSSTox_GSID_22089, F3385-6275, CAS-621-42-1, SMR000568485, acetyl-m-aminophenol, acetyl-2-aminophenol, Metacetamolo, 3-acetamido phenol, 3-acetylaminophenol, PubChem3835, Spectrum_000976, SpecPlus_000775, AC1L1YWF, AC1Q1KOL, Metacetamol [INN:BAN], Spectrum2_000517, Spectrum3_001262, Spectrum4_000086, Spectrum5_000701, ACMC-1BAS2, AC1Q5N4C, A7205_ALDRICH, CHEMBL9419, BSPBio_002824, KBioGR_000352, KBioSS_001456, SPECTRUM211175, MLS000881135, MLS000881183, MLS001065601, DivK1c_006871, N-(3-hydroxyphenyl)ethanamide, SCHEMBL181254, SPBio_000473, AC1Q1L10, ARONIS023443, V942ZCN81H, Acetamide,N-(3-hydroxyphenyl)-, CTK5B4406, KBio1_001815, KBio2_001456, KBio2_004024, KBio2_006592, KBio3_002324, N-(3-Hydroxy-phenyl)-acetamide, NSC3990, MolPort-001-766-013, HMS1923M09, Pharmakon1600-00211175, NSC-3990, STR00900, N-(3-hydroxyphenyl)ethanimidic acid, Tox21_111130, Tox21_200252, ANW-34077, BS-749, CCG-39594, LABOTEST-BB LT00005728, LABOTEST-BB LT03328299, LABOTEST-BB LT03329153, LABOTEST-BB LT03333227, NSC755827, SBB055395, STK949035, ZINC00001691, AKOS000442198, Tox21_111130_1, AB00216, AS00889, LS-1487, MCULE-1526482888, NE10160, NSC-755827, PS-4520, NCGC00091423-01, NCGC00091423-03, NCGC00091423-04, NCGC00091423-05, NCGC00091423-06, NCGC00091423-08, NCGC00257806-01, AJ-08071, AK-84439, KB-86424, ZB000392, KB-107493, ST2407372, TC-122822, TL8004047, FT-0614857, ST45052934, W7420, EN300-15588, 51233-EP2270006A1, 51233-EP2311824A1, A833608, BRD-K16474819-001-02-1, 3B3-032661, T0517-8613, InChI=1/C8H9NO2/c1-6(10)9-7-3-2-4-8(11)5-7/h2-5,11H,1H3,(H,9,10

Removed Synonyms

NEBS, N-(3-Hydroxyphenyl)urea, C8H9NO2, CID12124, H0188, 4-13-00-00977 (Beilstein Handbook Reference), C026137

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