Water → Tetradecylphenol

HRID 235715Notes

Reaction equation

HRID 235715 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:9][CH:8]=1.O>C(Cl)Cl>[CH2:13]([C:10]1[CH:9]=[CH:8][C:7]([OH:6])=[CH:12][CH:11]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 202187144-Methoxy-1-tetradecyl-benzene

Product 1

HCID 116800TetradecylphenolYield 101.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Boron tribromide was added dropwise, under argon to an about -78° C. solution of about 12.16 g of 4-methoxy-1-tetradecyl-benzene in about 125 ml of methylene chloride. The reaction was stirred for about 21/2 hours at about -78° C., then water was added dropwise, the organic layer separated, washed with sodium bicarbonate solution and evaporated, giving about 11.8 g of the desired title compound, mp 70°-71° C.

Workup

  1. customthe organic layer separated
  2. washwashed with sodium bicarbonate solution
  3. customevaporated

Sources & evidence

ORD record
ord-f9007c6b1efb48c18a61a71b6654494a
Source dataset
uspto-grants-1987_02
Patent number
US04640913

Reaction notes

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