4-Methoxybenzyl alcohol → 4-Methoxybenzyl 4-bromobutyrate

HRID 260829Notes

Reaction equation

HRID 260829 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.C(N(CC)CC)C.[Br:18][CH2:19][CH2:20][CH2:21][C:22](Cl)=[O:23]>ClCCl>[Br:18][CH2:19][CH2:20][CH2:21][C:22]([O:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:23]

Participants

5

Reactant 3

HCID 77384-Methoxybenzyl alcoholHCID 8471TriethylamineHCID 702254-Bromobutyryl chloride

Product 1

HCID 224004624-Methoxybenzyl 4-bromobutyrate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-methoxybenzyl alcohol and triethylamine in dichloromethane was added 4-bromobutyryl chloride at 0° C. The mixture was stirred at 0° C. for 30 minutes, and the solvent was evaporated. The residue was diluted with ethyl acetate, and the organic solution was washed with water and brine, dried over magnesium sulfate and concentrated. The concentrate was chromatographed on a silica gel column to give the object compound.

Workup

  1. customthe solvent was evaporated
  2. additionThe residue was diluted with ethyl acetate
  3. washthe organic solution was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was chromatographed on a silica gel column
  7. customto give the object compound

Sources & evidence

ORD record
ord-ff5a459a17154bdab92f3cdc6e0d786f
Source dataset
uspto-grants-1996_06
Patent number
US05530019

Reaction notes

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