Boron tribromide → Phenol, 2-hexadecyl-

HRID 235722Notes

Reaction equation

HRID 235722 reaction equation
[CH2:1]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23]C)[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][CH3:16].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23])[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][CH3:16]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 202186521-Hexadecyl-2-methoxybenzene

Product 1

HCID 117474Phenol, 2-hexadecyl-Yield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of about 14.94 g of 1-hexadecyl-2-methoxybenzene in methylene chloride, under argon, was cooled to about -78° C. and about 3.76 g of boron tribromide was added. The mixture was allowed to warm to room temperature, was then stirred for about 24 hours and quenched by the dropwise addition of ice-cold water. The mixture was then washed with sodium bicarbonate solution, dried and evaporated, giving about 14 g of the desired reagent, mp 54°-55° C.

Workup

  1. customquenched by the dropwise addition of ice-cold water
  2. washThe mixture was then washed with sodium bicarbonate solution
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-260062219e7143e7bf5357d86888479a
Source dataset
uspto-grants-1987_02
Patent number
US04640913

Reaction notes

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