Toluene → Methyl 16-bromohexadecanoate

HRID 1425662Notes

Reaction equation

HRID 1425662 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].[C:20]1(C)C=CC=CC=1.COC(OC)OC>CO>[CH3:20][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 1140TolueneHCID 9005Trimethyl orthoformateHCID 62039716-Bromohexadecanoic acid

Product 1

HCID 2736822Methyl 16-bromohexadecanoateYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

16-Bromohexadecanoic acid (6 g, 17.9 mmol) was dissolved in methanol (35 mL), toluene (100 mL) and trimethylorthoformate (20 mL). Amberlyst 15 was added and the mixture was stirred under nitrogen for 16 h at 55° C. The mixture was concentrated, and dissolved in methanol (ca. 50 mL) and DCM (30 mL). The resin was filtered off, and the filtrate was concentrated. The volume was increased to ca. 40 mL with methanol. Cooling produced crystals which were filtered off, washed with cold methanol and dried to yield white crystals (5.61 g, 90% yield).

Workup

  1. additionAmberlyst 15 was added
  2. concentrationThe mixture was concentrated
  3. dissolutiondissolved in methanol (ca. 50 mL)
  4. filtrationThe resin was filtered off
  5. concentrationthe filtrate was concentrated
  6. temperatureThe volume was increased to ca. 40 mL with methanol
  7. temperatureCooling
  8. customproduced crystals which
  9. filtrationwere filtered off
  10. washwashed with cold methanol
  11. customdried

Sources & evidence

ORD record
ord-7b5209de1f42442bb030fe1131b50b47
Source dataset
uspto-grants-2015_01
Patent number
US08933021B2

Reaction notes

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