Synthesis of salicylaldehyde

Preparation of salicylaldehyde

Preparation of salicylaldehyde

Preparation of salicylaldehyde

50 g of phenol and 160 g of caustic soda in 160 ml of water are heated to 50-60° C in a 1-litre flask on a water bath under a reflux. A thermometer dipping into the liquid is fitted to the flask. 75 g of chloroform are added, 10 c at a time, through the top of the condenser, the flask being well shaken after each addition. By alternate heating and cooling the temperature is kept at 65° C throughout. The whole is then refluxed for half an hour, the excess of chloroform removed on a water bath, and the residue carefully acidified with dilute sulfric acid and distilled in steam till no more oily drops pass over. The distillate is extracted with ether, and the extract shaken with twice its volume of a freshly prepared, nearly saturated solution of sodium hydrogen sulfite for a long time till no more crystals separate. The precipitated bisulfite compound is filtered off, washed free from traces of phenol with alcohol and decomposed by heating on a water bath with dilute sulfuric acid. The aldehyde which separates is extracted with ether, the extract washed with water and dehydrated over anhydrous sodium sulfate. The ether is removed on a water bath and the aldehyde distilled. Some p-hydroxybenzaldehyde remains in the flask after the steam distillation. tarry matter is removed by filtering hot through a moistened filter paper. The cold filtrate is extracted with ether, the extract dried over calcium chloride, the ether removed on a water bath, and the residue recrystallized from a small quantity of hot water containing sulfur dioxide. The yield of salicylaldehyde is  20%. p-Hydroxybenzaldehyde, 4% theoretical. Salicylaldehyde is cColourless fragrant oil, soluble in water; miscible in all proportions with alcohol and ether; b.p. 196.5° C; solidifies to large crystals at 0° C.  d=1.172 g/ml at 15° C.

Systematic organic chemistry, by W. M. Cumming, 105, 1937.

IUPAC Name

2-hydroxybenzaldehyde

InChI

InChI=1S/C7H6O2/c8-5-6-3-1-2-4-7(6)9/h1-5,9H

InChI Key

SMQUZDBALVYZAC-UHFFFAOYSA-N

Canonical SMILES

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

MeSH Synonyms

2-hydroxybenzaldehyde, salicylaldehyde, Salicylaldehyde ester

Depositor-Supplied Synonyms

SALICYLALDEHYDE, 2-Hydroxybenzaldehyde, 90-02-8, Salicylal, o-Hydroxybenzaldehyde, o-Formylphenol, 2-Formylphenol, Benzaldehyde, 2-hydroxy-, Salicylic aldehyde, Salicyladehyde, Salicylaldehyd, Salizylaldehyd, 2-HYDROXY-BENZALDEHYDE, Benzaldehyde, o-hydroxy-, 2-hydroxy benzaldehyde, Benzaldehyde, hydroxy-, NSC 49178, UNII-17K64GZH20, FEMA No. 3004, CCRIS 7451, CHEMBL108925, HSDB 721, CHEBI:16008, SMQUZDBALVYZAC-UHFFFAOYSA-N, EINECS 201-961-0, BRN 0471388, AI3-02174, DSSTox_CID_1792, DSSTox_RID_76329, 2,4-Cyclohexadien-1-one, 6-(hydroxymethylene)-, DSSTox_GSID_21792, CAS-90-02-8, 111268-93-0, 28777-87-9, NK, salicyl aldehyde, Hydroxybenzaldehyde, hydroxy benzaldehyde, 2-hyroxy-benzaldehyde, 2-oxidanylbenzaldehyde, Salicylaldehyde, 8CI, 2- hydroxybenzaldehyde, ACMC-20me6q, AC1L1NRV, WLN: VHR BQ, bmse000677, S356_ALDRICH, PHENOXY, 2-FORMYL-, SCHEMBL15395, KSC204S9R, 84160_ALDRICH, W300403_ALDRICH, AC1Q6Q92, AC1Q78A0, 03273_FLUKA, 84160_FLUKA, CTK0D4077, CTK1A4998, FEMA 3004, Poly(oxy-1,2-phenylenecarbonyl), MolPort-000-871-199, 17K64GZH20, BB_SC-9449, ZINC896073, ACMC-209783, NSC49178, Tox21_201737, Tox21_302929, ANW-13633, AR-1E1826, BBL027432, BDBM50139367, NSC-49178, NSC187662, RW2543, SBB040225, ZINC00896073, AKOS000119187, AS03003, EBD2205190, LS-3090, MCULE-8965879140, NSC-187662, RL05659, RTR-038301, TRA0028440, NCGC00249108-01, NCGC00256460-01, NCGC00259286-01, AJ-24221, AK134917, AN-24183, K615, OR012022, OR185321, OR249340, OR282459, OR369093, SC-18113, ZB015070, KB-230927, ST2410040, TR-038301, FT-0648915, S0004, S0275, ST50213374, 7293-EP2270014A1, 7293-EP2281563A1, 7293-EP2301933A1, 7293-EP2308872A1, 7293-EP2311807A1, 7293-EP2311827A1, 7293-EP2316459A1, 7293-EP2316829A1, C06202, H-3700, 96428-EP2295429A1, 96428-EP2305629A1, 116358-EP2374783A1, 116358-EP2377841A1, 4-08-00-00176 (Beilstein Handbook Reference), A843413, I01-4510, BENZALDEHYDE,2-HYDROXY-, LITHIUM SALT (1:1), 3B3-028928, InChI=1/C7H6O2/c8-5-6-3-1-2-4-7(6)9/h1-5,9, 27761-48-4

Removed Synonyms

CFM 4, CID6998, c0337, SAH, 100-83-4, 331458-02-7

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