Methods for the synthesis of 13C labeled iodotridecane and use as a reference standard

A process for preparing a 13C labeled haloalkane as represented by Formula (i):

• wherein R is a C1-C28 carbon chain, X is a halogen, and the compound of Formula (i) is 13C labeled at one or more of the carbon atoms labeled with an asterisk, the process comprising:
• (a) protecting the primary alcohol present in 13C labeled propargyl alcohol by ether bond formation to obtain a compound of Formula (ii):
• wherein the 13C labeled propargyl alcohol is labeled at C1, C2 or C3 thereof, or a combination thereof, and the compound of Formula (ii) is 13C labeled at one or more of the carbon atoms labeled with an asterisk;
• (b) alkylating the compound of Formula (ii) with X—R, wherein R is as defined above, and X is a halogen, to obtain a compound as represented by Formula (iii):
• wherein the compound of Formula (iii) is 13C labeled at one or more of the carbon atoms labeled with an asterisk;
• (c) hydrogenating the compound of Formula (iii) to obtain a compound as represented by Formula (iv):
• wherein the compound of Formula (iv) is 13C labeled at one or more of the carbon atoms labeled with an asterisk;
• (d) removing the protecting group in the compound of Formula (iv) to obtain the compound of Formula (v):
• wherein the compound of Formula (v) is 13C labeled at one or more of the carbon atoms labeled with an asterisk;
• and
• (e) halogenating the primary alcohol present in the compound represented by Formula (v) to obtain the compound of Formula (i).