Carbinol

Normal butyl alcohol, propyl carbinol, n-butanol, 1-buianol, CH3CH2CH2CH2OH. B.p. 117 C. Manufactured by reduction of crotonaldehyde (2-buienal) with H2 and a metallic catalyst. Forms esters with acids and is oxidized first to butanal and then to butanoic acid. U.S. production 1978 300 000 tonnes. 

Isobutyl alcohol, isobutanol, 2-methyl-propanol, isopropyl carbinol, Me2CHCH20H. B.p. 108°C. Occurs in fusel-oil. Oxidized by potassium permanganate to 2-methyl-propanoic acid dehydrated by strong sulphuric acid to 2-methylpropene. 

Tertiary butyl alcohol, trimethyl carbinol, tertiary butanol. 2-methyl-2-propanol, Me3COH. Colourless prisms, m.p. 25°C, b.p. 83°C. Prepared by absorbing isobutene (2-methylpropene) in sulphuric acid, neutralizing and steam distilling the liquor. Converted to isobutene by heating with oxalic acid. Potassium-/-buloxide is a very strong base. 

Michler s hydrol, bis(p-dinnethylaminopbenyl)-carbinol, Cj H22N20. Colourless crystals m.p. 96 C. 

Triphenyl-carbinol, (C6H5)3COHy from Ethyl Benzoate and Phenyl Magnesium Bromide. (Grignard Reaction 6 (a).)... 

Fit securely to the lower end of the condenser (as a receiver) a Buchner flask, the side-tube carrying a piece of rubber tubing which falls well below the level of the bench. Steam-distil the ethereal mixture for about 30 minutes discard the distillate, which contains the ether, possibly a trace of unchanged ethyl benzoate, and also any biphenyl, CeHs CgHs, which has been formed. The residue in the flask contains the triphenyl carbinol, which solidifies when the liquid is cooled. Filter this residual product at the pump, wash the triphenyl-carbinol thoroughly with water, drain, and then dry by pressing between several layers of thick drying-paper. Yield of crude dry product, 8 g. The triphenyl-carbinol can be recrystallised from methylated spirit (yield, 6 g.), or, if quite dry, from benzene, and so obtained as colourless crystals, m.p. 162. ... 

Steam-distil the ethereal solution and discard the distillate. The residue in the flask is triphenyl-carbinol and solidifies on cooling. Filter at the pump, wash with water, drain and dry. Yield of crude product 0 6 g. Recrystallise when dry from benzene to obtain colourless crystals m.p. 162°. 

B. 2-Pentene. Proceed as in A, but use the following quantities 50 ml. of water and 50 ml. of concentrated sulphuric acid 40 g. of methyl n-propyl carbinol (4). Collect the distillate passing over below 40°. Pure 2-pentene boils at 36-5°. 

Methyl n-amyl ketone Methyl n-amyl carbinol (2-heptanol)... 

Methyl n-butyl ketone Methyl n.butyl carbinol... 

Use the apparatus detailed in Section 111,20. Dissolve 100 g. (123 ml.) of methyl n-butyl ketone (2-hexanone) (Section 111,152) in 750 ml. of ether and add 150 ml. of water. Introduce 69 g. of clean sodium in the form of wire (or small pieces) as rapidly as possible the reaction must be kept under control and, if necessary, the flask must be cooled in ice or in running water. When all the sodium has reacted, separate the ethereal layer, wash it with 25 ml. of dilute hydrochloric acid (1 1), then with water, dry with anhydrous potassium carbonate or with anhydrous calcium sulphate, and distil through a fractionating column. Collect the fraction of b.p. 136-138°. The yield of methyl n-butyl carbinol (2-hexanol) is 97 g. 

Dimethyl n-propyl carbinol, CH3(CH2)2COH(CH3)2. From n-propyl magnesium bromide and acetone. Collect the tertiary alcohol at 121-124°. 

Dimethyl ethyl carbinol (2-methy 1-2-butanol or amyl alcohol), CH3CHjCOH(CH3).2. From ethyl propionate and methyl magnesium iodide. Collect the tertiary alcohol at 100-102°. 

Methyl n-ptopyl carbinol (6) Cetyl alcohol (11) Ethyl celloBOlve (16) Butyl carbitol ... 

Diethyl carbinol (7) Stearyl alcohol (12) Butyl cellosolve (17) 2 Aminoethyl alcohol ... 

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