Synthesis of 1-heptanol

Preparation of 1-heptanol

Preparation of 1-heptanol by reduction of 1-heptanal with iron

Preparation of 1-heptanol by reduction of 1-heptanal with iron

Preparation of 1-heptanol by reduction of 1-heptanal with iron

To a 3-liter round-bottomed flask, fitted with a mechanical stirrer and a short reflux condenser, 450 grams of grease-free iron filings, 750 ml of glacial acetic acid, 750 ml of water, and 137.5 ml (or 112.5 grams) of freshly distilled (b.p. 154-156° C) 1-heptanal (n-heptaldehyde) are placed. The mixture is heated with stirring, for 2-4 hours. If the frothing is considerable during the reduction reaction, the mixture is cooled. The 1-heptanol is steam distilled directly from the flask until no more oily drops pass over (usually about 2 liters of distillate). The oily 1-heptanol us separated and further small quantity may be obtained by saturating the aqueous layer with sodium chloride. The crude 1-heptanol is heated with 250 ml of 20% sodium hydroxide solution with stirring on the water bath for 2 hours in order to hydrolyze the small proportion of 1-heptyl acetate. The solution is cooled and the oil is separated (a further small quantity of 1-heptanol may be obtained from the alkaline solution by mixing it with 50 ml of water and distilling: the distillate is saturated with sodium chloride the oil separated, dried and distilled). 1-Heptanol is dried with a little anhydrous potassium carbonate or anhydrous calcium sulfate and distilled by collecting the fraction boiling at 173-176° C. The yield of 1-heptanol is 90 grams.

A text book of practical organic chemistry, by A. I. Vogel, 251, 1974

Preparation of 1-heptanol by reduction of 1-heptanal with lithium aluminum hydride

Preparation of 1-heptanol by reduction of 1-heptanal with lithium aluminum hydride

Preparation of 1-heptanol by reduction of 1-heptanal with lithium aluminum hydride

2-liter three-necked flask is fitted with a stirrer, a reflux condenser, a dropping funnel, and calcium chloride tube. A solution of 19 g of lithium aluminum hydride dissolved in 600 ml of ether is placed in the reaction flask. 200 g of 1-heptanal (n-heptaldehyde) are then added, with stirring, at such a rate that the mixture continues to boil. Whilst stirring is continued, water is dropped in, cautiously and with strong cooling, to decompose the excess of lithium aluminum hydride. When all lithium aluminum hydride is neutralized the mixture is poured into ice-water and treated with 10% sulfuric acid. After removal of the ethereal layer, the aqueous solution is extracted additionally with ether. The ethereal extracts are combined, dried and evaporated, the residue of 1-heptanol is distilled through a column. The yield of  1-heptanol is 86% (b.p. 175-175.5 °C/750mm).

R. F. Nystrom, et al. J. Amer. Chem. Soc, 69, 1197, (1947).

R. F. Nystrom, et al. J. Amer. Chem. Soc,  69, 2548, (1947).

R. F. Nystrom, et al. J. Amer. Chem. Soc, 70, 3738, (1948).

IUPAC Name

heptan-1-ol

InChI

InChI=1S/C7H16O/c1-2-3-4-5-6-7-8/h8H,2-7H2,1H3

InChI Key

BBMCTIGTTCKYKF-UHFFFAOYSA-N

Canonical SMILES

CCCCCCCO

MeSH Synonyms

1 Heptanol, 1-Heptanol, Alcohol, Heptyl, Heptanol, Heptyl Alcohol, n Heptanol, n-Heptanol

Depositor-Supplied Synonyms

1-HEPTANOL, Heptan-1-ol, Heptyl alcohol, n-Heptanol, Heptanol, n-Heptyl alcohol, Enanthic alcohol, 111-70-6, Gentanol, 1-Hydroxyheptane, n-Heptan-1-ol, Enanthyl alcohol, Hydroxyheptane, Hexyl carbinol, Hydroxy heptane, C7 alcohol, n-Heptanol-1, Alcohol C-7, Fatty alcohol(C7), Pri-n-heptyl alcohol, Heptyl alcohol, primary, FEMA Number 2548, NSC 3703, Heptyl alcohol (natural), N-Heptanol-1 [French], HEPTYL ALCOHOL, N-, l’Alcool n-heptylique primaire, UNII-8JQ5607IO5, FEMA No. 2548, HSDB 1077, NSC3703, BBMCTIGTTCKYKF-UHFFFAOYSA-N, EINECS 203-897-9, BRN 1731686, l’Alcool N-heptylique primaire [French], AI3-15363, DSSTox_CID_1937, DSSTox_RID_76413, DSSTox_GSID_21937, CAS-111-70-6, HE4, heptanol-1, 1-heptyl alcohol, Alcohol C7, Heptane-1-ol, C-7 alcohol, 1-Hept, ACMC-1BWJZ, AC1L1QBW, AC1Q7CPB, n-C7H15OH, SCHEMBL2077, H2805_ALDRICH, WLN: Q7, KSC175K2D, 51778_ALDRICH, W254800_ALDRICH, CHEMBL273459, Jsp000878, 51778_FLUKA, 72954_FLUKA, CTK0H5521, MolPort-001-779-717, 8JQ5607IO5, LTBB001122, NSC-3703, EINECS 258-615-7, Tox21_201247, Tox21_303470, ANW-16310, AR-1C3366, LMFA05000122, STL280281, AKOS000120104, LS-2790, MCULE-5882959353, RTR-002298, TRA0005177, NCGC00249005-01, NCGC00257506-01, NCGC00258799-01, AN-43084, TR-002298, FT-0607877, 184020-EP2269986A1, 184020-EP2272817A1, 184020-EP2380568A1, 4-01-00-01731 (Beilstein Handbook Reference), A802399, 3B4-1502, S14-1469, 3B1-000443, InChI=1/C7H16O/c1-2-3-4-5-6-7-8/h8H,2-7H2,1H

Removed Synonyms

n Heptanol, B-Nonylglucoside, Alcohol, Heptyl, 1 Heptanol, CID8129, (Hydroxyethyloxy)tri(Ethyloxy)octane, H0033, D019850, 53535-33-4, 5444-82-6, BNG, C8E

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