Water → 3-Tetradecylphenol

HRID 1885890Notes

Reaction equation

HRID 1885890 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br.O>C(Cl)Cl>[CH2:9]([C:5]1[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 12517105HCID 12517105, compound

Product 1

HCID 144404953-Tetradecylphenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 136.8 g of 3-methoxy-1-tetradecylbenzene in 600 ml of methylene chloride, cooled to -78° C., under inert gas, was added dropwise a solution of 112.8 g of boron tribromide in 100 ml of methylene chloride. The mixture was kept at -78° C. for 1 hour then allowed to warm slowly to room temperature followed by stirring for 16 hours. The mixture was cooled to 0° C. and cold water added dropwise. The organic layer was separated and washed with aqueous sodium bicarbonate, dried and the solvent evaporated. The residue was poured onto crushed ice and 107 g of the desired product collected as a white solid, m.p. 38°-40° C.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customThe organic layer was separated
  3. washwashed with aqueous sodium bicarbonate
  4. customdried
  5. customthe solvent evaporated
  6. additionThe residue was poured
  7. customonto crushed ice and 107 g of the desired product
  8. customcollected as a white solid, m.p. 38°-40° C.

Sources & evidence

ORD record
ord-40ef46c1c27448679a3226a664ee0aa0
Source dataset
uspto-grants-1992_09
Patent number
US05147864

Reaction notes

Loading…