Synthesis of benzoin

Preparation of benzoin

Alternative Names: 2-Hydroxy-1,2-diphenylethanone; 2-Hydroxy-2-phenylacetophenone; Benzoylphenylcarbinol; Bitter almond oil camphor;

Preparation of benzoin

Preparation of benzoin

50 g benzaldehyde are boiled with 5 g potassium cyanide, 100 g alcohol, and 100 g water for 15-20 minutes under reflux condenser. On cooling the benzoin separates out in a crystalline mass. It is filtered at and recrystallized from alcohol with the addition of activated charcoal. The first mother liquor is again heated to boiling with about 2 g potassium cyanide, and the benzoin formed is separated as before. Yield about 45 g, melting point 134° C.

Introduction to the preparation of organic compounds, E. Fisher, 62, 1909

IUPAC Name

2-hydroxy-1,2-diphenylethanone

InChI

InChI=1S/C14H12O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13,15H

InChI Key

ISAOCJYIOMOJEB-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)C(C(=O)C2=CC=CC=C2)O

MeSH Synonyms

2 hydroxy 1,2 diphenylethanone, 2-hydroxy-1,2-diphenylethanone, Benzoin

Depositor-Supplied Synonyms

BENZOIN, 2-Hydroxy-1,2-diphenylethanone, 119-53-9, 2-Hydroxy-2-phenylacetophenone, Benzoylphenylcarbinol, Bitter almond oil camphor, (+-)-Benzoin, Benzoin tincture, Ethanone, 2-hydroxy-1,2-diphenyl-, alpha-Hydroxybenzyl phenyl ketone, Phenylbenzoyl carbinol, 2-hydroxy-1,2-diphenylethan-1-one, DL-BENZOIN, alpha-Hydroxy-alpha-phenylacetophenone, NCI-C50011, Acetophenone, 2-hydroxy-2-phenyl-, 579-44-2, Phenyl-alpha-hydroxybenzyl ketone, 2-hydroxy-1,2-diphenyl-ethanone, NSC 8082, Bitter-almond-oil camphor, Wy 42956, Benzoin extract (resinoid), CCRIS 75, Hydroxy-2-phenyl acetophenone, FEMA No. 2132, CCRIS 6696, CHEMBL190677, HSDB 384, CHEBI:17682, 2-hydroxy-1,2-diphenyl ethanone, ISAOCJYIOMOJEB-UHFFFAOYSA-N, Ketone, alpha-hydroxybenzyl phenyl, Phenyl-.alpha.-hydroxybenzyl ketone, Benzoin (VAN), EINECS 204-331-3, EINECS 209-441-5, Ketone, .alpha.-hydroxybenzyl phenyl, Fenyl-alpha-hydroxybenzylketon [Czech], BRN 0391839, NCGC00091396-02, WY-42956, (1)-2-Hydroxy-1,2-diphenylethan-1-one, .alpha.-Hydroxy-.alpha.-phenylacetophenone, AI3-00851, DSSTox_CID_144, DSSTox_RID_75397, DSSTox_GSID_20144, CAS-119-53-9, benzoine, Aerozoin, desyl alcohoe, PhCH(OH)COPh, PhCOCH(OH)Ph, PubChem20784, ACMC-20apg7, AC1L1QWZ, (.+/-.)-Benzoin, WLN: QYR&VR, SCHEMBL145, Benzoin (VAN) (8CI), Persian balsam (Salt/Mix), B8681_ALDRICH, Oprea1_687165, Fenyl-alpha-hydroxybenzylketon, KSC175O0J, MLS002152893, W213209_ALDRICH, hydroxy-2-pheny l acetophenone, 399396_ALDRICH, CCRIS 9123, Fenyl-.alpha.-hydroxybenzylketon, BDBM22728, CTK0H5704, NSC8082, Alpha-hydroxy-a-phenylacetophenone, MolPort-001-768-888, BB_NC-0133, HMS3039I03, 2-hydroxy-1,2-di(phenyl)ethanone, .alpha.-Hydroxybenzyl phenyl ketone, ACN-S002455, NSC-8082, Tox21_111126, Tox21_201888, Tox21_302790, ANW-17343, BBL011613, DNC005432, LS-618, SBB012413, STK358785, AKOS000118894, AKOS016038141, Tox21_111126_1, MCULE-7039379354, NE10325, RL00758, RP26678, RTR-034358, 2-Hydroxy-2-phenylacetophenone; Benzoin, NCGC00091396-01, NCGC00091396-03, NCGC00091396-05, NCGC00256433-01, NCGC00259437-01, AC-11139, AK106185, AN-22805, AN-46054, KB-68829, OR009988, OR184283, OR288515, SMR001224505, ST069353, AB1002600, KB-173021, LS-163970, TR-034358, B0079, B0222, ST24040660, C01408, 4-08-00-01279 (Beilstein Handbook Reference), AE-848/06163047, Ethanone, 2-hydroxy-1,2-diphenyl-, (.+/-.)-, S01-0573, T7103996, I14-19964, I14-53965, 3B3-017721, Ethanone, 2-hydroxy-1,2-diphenyl-, mixt. with aloe, storax and Tolu Balsam, tincture, 8050-35-9

Removed Synonyms

Anisoin, Sumatra benzoin, Resin benjamin, Styrax benzoin, Benzoin resin, Resin benzoin, Benjamin gum, Benzoin Malasia, Benzoin Sumatra, Siam benzoin, Benzoin gum, Benzoin usp, Gum sumatra, Benzoin absolute, Benzoin resinoid, Benzoin Siam, Gum Benjamin, Gum benzoin siam, Benzoin gum, Sumatra, Ethanone,2-diphenyl-, 2,2′-Thenoin, GUM BENZOIN, Benzoin resinoid, Siam, (S)-(+)-Benzoin, Hyperabsolute benzoin, Siam, UNII-L7J6A1NE81, FEMA No. 2133, HSDB 1929, CID8400, EINECS 232-523-7, 5928-67-6, |A-Hydroxy-|A-phenylacetophenone; |A-Hydroxybenzyl phenyl ketone; 2-Hydroxy-2-phenylacetophenone, 119-52-8, 27761-02-0, 9000-05-9, 9000-73-1, 91845-21-5

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