Synthesis of oleyl alcohol

Preparation of oleyl alcohol

Alternative Names: Cis-9-Octadecen-1-ol; Conditioner 1; Dermaffine; Lancol; Ocenol;

Preparation of oleyl alcohol

Preparation of oleyl alcohol

200 g of distilled ethyl oleate and 1.5 liter of absolute alcohol are placed in a 5-liter round-bottomed flask under a wide reflux condenser. The alcohol has been previously dried over calcium and is distilled from aluminum tert-butoxide directly into the reaction flask. 80 g of sodium are added gradually through the reflux condenser at such a rate that vigorous reaction ensues, the flask being occasionally shaken. When the main reaction has ended, additionally  200 ml of absolute alcohol are added and the mixture is heated on the steam-bath until all the sodium is consumed. Then 500 ml of water are added and the heating continued for a further hour to hydrolyse unchanged ester. The unsaponifiable fraction is extracted with ether. The ether extract is washed with 1 % potassium hydroxide solution and then with water until free from alkali and is dried over sodium sulfate. The ether is distilled off and the residue is fractionally distilled at 150-152°/1 mm yielding 49-51 % (or 84-89 g) of oleyl alcohol .

Org. Syn., Coll. Vol. III , 671 (1955).

IUPAC Name

(Z)-octadec-9-en-1-ol

InChI

InChI=1S/C18H36O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h9-10,19H,2-8,11-18H2,1H3/b10-9-

InChI Key

ALSTYHKOOCGGFT-KTKRTIGZSA-N

Canonical SMILES

CCCCCCCCC=CCCCCCCCCO

Isomeric SMILES

CCCCCCCC/C=C\CCCCCCCCO

MeSH Synonyms

cis-9-octadecen-1-ol, Oleol, oleyl alcohol, oleyl alcohol, (Z)-isomer

Depositor-Supplied Synonyms

OLEYL ALCOHOL, cis-9-Octadecen-1-ol, Conditioner 1, Dermaffine, Lancol, Ocenol, Novol, Oceol, Oleol, Satol, Oleic alcohol, Oleo alcohol, Crodacol-O, Loxanol M, (Z)-octadec-9-en-1-ol, Atalco O, Siponol OC, Sipol O, Cachalot O-1, Cachalot O-3, Cachalot O-8, H.D. eutanol, HD-Ocenol K, Loxanol 95, Unjecol 50, Unjecol 70, Unjecol 90, Cachalot O-15, cis-9-Octadecenyl alcohol, Crodacol A.10, Octadecenol, Unjecol 110, HD oleyl alcohol CG, Oleoyl alcohol, Olive alcohol, 0leyl alcohol, (9Z)-octadec-9-en-1-ol, Adol 34, Adol 80, Adol 85, Adol 90, 9-Octadecen-1-ol, (Z)-, Adol 320, Adol 330, Adol 340, HD-Ocenol 90/95, (Z)-9-Octadecen-1-ol, HD oleyl alcohol 70/75, HD oleyl alcohol 80/85, HD oleyl alcohol 90/95, Oleylalcohol, 9-Octadecen-1-ol, (9Z)-, cis-9-octadecenol, cis-octadecen-1-ol, (Z)-9-octadecenol, 143-28-2, (Z)-Octadec-9-enol, 9-Octadecen-1-ol, cis-, UNII-172F2WN8DV, CHEBI:73504, HSDB 6484, ALSTYHKOOCGGFT-KTKRTIGZSA-N, EINECS 205-597-3, 9-Octadecen-1-ol, NSC 10999, AI3-07620, 9-Octadecenol, HD-Eutanol, Octadec-9Z-enol, Witcohol 85, Witcohol 90, Unjecol 90N, Unjecol 90NR, Oleyl alcohol (NF), 9Z-Octadecen-1-ol, Z-9-Dodecen-1-ol, ( Z)-9-octadecenol, Witcohol 85 (TN), (9Z)-octadecen-1-ol, cis-9-0ctadecen-1-ol, AC1NR4KM, DSSTox_CID_2010, Octadeca-9-cis-en-1-ol, cis-.DELTA.9-Octadecenol, SCHEMBL5668, (9Z)-9-Octadecen-1-ol, (Z)-octadeca-9-en-1-ol, DSSTox_RID_76459, DSSTox_GSID_22010, O8880_SIGMA, 172F2WN8DV, 369314_ALDRICH, (9Z)-9-Octadecen-1-ol #, Octadec-9-en-1-ol, (Z)-, CHEMBL2105350, MolPort-003-931-111, 506-42-3, NSC10999, Tox21_200111, 7025AA, LMFA05000213, NSC-10999, AKOS004910411, NCGC00164365-01, NCGC00164365-02, NCGC00257665-01, AK114224, AN-23262, CAS-143-28-2, LP074259, LS-97766, SC-19456, DB-007794, KB-212151, FT-0081274, O0058, ST51056619, D05245, 3B3-033001, 3164D881-7E14-4979-9E60-58DDC0468323, 8014-60-6, 8029-00-3, 8038-59-3, 84286-21-5

Removed Synonyms

Elaidyl alcohol, Octadec-9-en-1-ol, CID5284499

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