Methanol → Methyl 16-bromohexadecanoate

HRID 2174348Notes

Reaction equation

HRID 2174348 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18].CO.[CH3:22]OC(OC)OC>C1(C)C=CC=CC=1>[CH3:22][O:18][C:17](=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1]

Participants

5

Reactant 3

HCID 887MethanolHCID 9005Trimethyl orthoformateHCID 62039716-Bromohexadecanoic acid

Product 1

HCID 2736822Methyl 16-bromohexadecanoateYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 16-bromohexadecanoic acid (15.5 g, 46.2 mmol), MeOH (100 ml), PhMe (30 ml), trimethylorthoformate (30 ml), and polystyrene-bound benzenesulfonic acid (3.6 g) was stirred at 55° C. After 69 h the mixture was filtered through celite and the filtrate was concentrated to yield 16.85 g of an oil (100% yield).

Workup

  1. filtrationAfter 69 h the mixture was filtered through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ee54e57f8bc94e819d49a898e1aa1434
Source dataset
uspto-grants-2015_06
Patent number
US09061067B2

Reaction notes

Loading…