278 REPORTS ON THE STATE OF SCIENCE. 
Acree! shows that the action with a diketone may be regulated so 
that either one or both of the carbonyl groups react. It is possible, for 
example, to obtain from benzil, C;H,.CO.CO.C,H;, either the keto- 
alcohol, phenylbenzoin, (C,H;),C(OH).CO.C;H;, or benzpinacone, 
(C,H,),C(OH) . C(OH)(C,H,)» 
The optically active glycol, tetraphenylerythritol, 
(C,H,).C(OH) . CH(OH) . CH(OH) . C(OH)(C,H,), 
has been obtained by P. F. Frankland and Twiss? by the action of 
magnesium phenyl bromide on dimethyl d-tartrate. 
(c) Primary alcohols.--The Grignard reagent is not so useful for the 
preparation of primary alcohols as for the classes to which reference has 
been made. When a current of dry oxygen is passed into an ethereal 
solution of the Grignard reagent, oxidation takes place and a primary 
alcohol is formed when water is added,? e.9., 
C,H, .CH,MgCl + O = C,H,. CH,OMgCl 
C,H, .CH,OMgCl + H,O = C,H,.CH,OH + MgClOH 
the yield of benzyl] alcohol being 80 per cent. 
When the Grignard reagent is heated for several days with trioxy- 
methylene the primary alcohols are obtained, sometimes in good yield ; 
thus n-propyl alcohol is obtained from magnesium ethyl bromide.’ 
Ethylene oxide may also be converted into primary alcohols,’ for 
example, 2-butyl alcohol is obtained from magnesium ethyl bromide.° 
H, CyinrGH O,H 
Sokme< pe So iat 
\br CH \MgBr 
+ C,H,.CH,.CH,.OMgBr + 0,H,.CH,.CH,OH 
The action of ethylene monochlorohydrin on a magnesium organic 
compound takes place in two phases. The hydroxy-group is first acted 
on in the cold :— 
RMgX + CH,Cl.CH,OH = RH + CH,Cl. CH,OMgX 
On the addition of a second molecular proportion, R’/MgX, which 
may be different from the first, a vigorous reaction again takes pluce 
when the ether is distilled off from the mixture and the temperature 
gradually raised :— 
R/MgX’ + CH,Cl. CH,OMgX = MgX'Cl + R’.CH,.CH,.OMgX 
Phenylethy] alcohol, C;H,;.CH, .CH,OH, is readily obtained in this 
manner from magnesium phenyl bromide.’ 
(d) Phenols.—Bodroux*® applied for the preparation of phenols the 
method which Bouveault used for primary alcohols (/oc. cit.), but the 
yields obtained were very small. ‘The method appears, however, to be a 
' Ber., 1904, 37, 2753. 2 Trans. Chem. Soc., 1904, 85, 1666. 
* Bouveault, Bull. Soc. Chim., 1903 [31, 29, 1051. 
* Grignard and Tissier, Compt. rend., 1902, 184, 107. 
5 Blaise, idid., 1902, 184, 551. 
® Grignard, ibid., 1903, 1386, 1260; Budll. Soc. Chim., 1903 [3], 29, 944. 
7 Grignard, Compt. rend., 1905, 141, 44; Bull. Soc. Chim., 1907 [8], 10, 23. 
5 Compt. rend., 1903, 186, 158; Bull. Soc. Chim., 1904 [3], 81, 33. 
