Methanol → Methyl 11-bromoundecanoate

HRID 653348

Reaction equation

HRID 653348 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[Cl-].[Ca+2].[Cl-].[CH3:18]O>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:18])=[O:13]

Participants

4

Reactant 3

HCID 887MethanolHCID 1781211-Bromoundecanoic acidHCID 5284359Calcium Chloride

Product 1

HCID 223913Methyl 11-bromoundecanoateYield 84%

Procedure

11-Bromoundecanoic acid (commercial material, 25.0 g, 94 mmol), Duolite H+ resin (10 g), calcium chloride (26.2 g, 94 mmol) and methanol (700 ml) were stirred for 15 h. The methanol was removed and dichloromethane was added. The mixture was washed with water, dried (Na2SO4) and concentrated. Distillation gave pure 103 (22.0 g, 84%) with b.p. 103°-104° (2×10-2 torr). 1H-NMR (CDCl3, Me4Si) δ 3.67 (s, 3H, MeO), 3.41 (t, 2H, J=6.8 Hz, Br--CH2), 2.31 (t, 2H, J=7.3 Hz, CH2CO).

Workup

  1. customThe methanol was removed
  2. additiondichloromethane was added
  3. washThe mixture was washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. distillationDistillation

Sources & evidence

ORD record
ord-602b2bdb47f54c15b743da6bba95f29f
Source dataset
uspto-grants-1987_06
Patent number
US04675392

Linked notes

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