Synthesis of propionic anhydride

Preparation of propionic anhydride

Propionic anhydride could be prepared similarly as acetic anhydride.

Preparation of propionic anhydride

Preparation of propionic anhydride

To the round bottom flask fitted with dropping 20 g of dry propionic acid are placed. From dropping funnel slowly 17.5 g of oxalyl chloride are added. During the addition of oxalyl chloride hydrogen chloride gas slowly evolved. The the reaction mixture was gently refluxed and the reaction product distilled yielding 9 g of the anhydride with boiling point 167-170°. The yield of anhydride was 51% the of theory, boiling point according to literature is 168° C.

Oxalyl chloride and oxalyl bromide as reagents in organic chemistry, L.H. Ulich, 23, 1918,

IUPAC Name

propanoyl propanoate

InChI

InChI=1S/C6H10O3/c1-3-5(7)9-6(8)4-2/h3-4H2,1-2H3

InChI Key

WYVAMUWZEOHJOQ-UHFFFAOYSA-N

Canonical SMILES

CCC(=O)OC(=O)CC

MeSH Synonyms

propanoic anhydride, propionic anhydride

Depositor-Supplied Synonyms

PROPIONIC ANHYDRIDE, Propanoic anhydride, propanoyl propanoate, 123-62-6, Propanoic acid, anhydride, Methylacetic anhydride, Propionyl oxide, Propionic acid anhydride, Caswell No. 708, Propanoic acid, 1,1′-anhydride, Anhydrid kyseliny propionove, UNII-E3A2VV18E6, HSDB 1215, WYVAMUWZEOHJOQ-UHFFFAOYSA-N, EINECS 204-638-2, Anhydrid kyseliny propionove [Czech], SBB060267, UN2496, EPA Pesticide Chemical Code 077704, BRN 0507066, AI3-26975, Propanoicanhydride, propanoic acid anhydride, ACMC-209apd, DSSTox_CID_7007, AC1L1L9M, SCHEMBL9276, DSSTox_RID_78279, DSSTox_GSID_27007, P51478_ALDRICH, KSC490Q0R, PROPANOIC ACID,ANHYDRIDE, 240311_ALDRICH, E3A2VV18E6, Jsp001584, C2H5C(O)OC(O)C2H5, CHEMBL3186472, CTK3J0808, propanoic acid 1-oxopropyl ester, PROPIONIC ANHYDRIDE, PRACT, MolPort-001-769-232, Tox21_201029, ANW-18143, STL356492, AKOS015918323, AN-5887, MCULE-4790806387, RP19904, RTR-003704, UN 2496, NCGC00248900-01, NCGC00258582-01, AK165598, CAS-123-62-6, KB-80121, SC-26875, DB-041737, LS-124892, Propionic anhydride [UN2496] [Corrosive], TR-003704, FT-0631715, P0513, Propionic anhydride [UN2496] [Corrosive], ST51046486, 40840-EP2272841A1, 40840-EP2277878A1, 40840-EP2277880A1, 40840-EP2289885A1, 40840-EP2289894A2, 40840-EP2292610A1, 40840-EP2308833A2, 40840-EP2311818A1, 40840-EP2311830A1, 4-02-00-00722 (Beilstein Handbook Reference), A805127, I14-8086, 3B3-023563, InChI=1/C6H10O3/c1-3-5(7)9-6(8)4-2/h3-4H2,1-2H

Removed Synonyms

CID31263

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