Potassium Carbonate → Benzyl 2-hydroxy-4-(2-methylallyloxy)benzoate

HRID 1292022

Reaction equation

HRID 1292022 reaction equation
[OH:1][C:2]1[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:3]=1[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[C:19](=O)([O-])[O-].[K+].[K+].C[CH:26]=[CH:27][CH2:28]Cl>CN(C=O)C>[OH:1][C:2]1[CH:17]=[C:16]([O:18][CH2:19][C:27]([CH3:28])=[CH2:26])[CH:15]=[CH:14][C:3]=1[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11589Crotyl chlorideHCID 7500968Benzyl 2,4-dihydroxybenzoate

Product 1

HCID 21829741Benzyl 2-hydroxy-4-(2-methylallyloxy)benzoateYield 57.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 17 g of benzyl 2,4-dihydroxybenzoate (0.07 mol) and 10 g of potassium carbonate (0.077 mol) in 60 ml of DMF brought to 70° C. were added 6.81 ml of methyallyl chloride (0.07 mol) dropwise over 1 hour. The mixture was left at 70° C. for 2 hours. It is cooled to about 40° C. and the salts are filtered off. The salts were washed with DMF. The liquids were combined, and the solvent was evaporated off. A brown oil was obtained which was purified on silica (eluent: 70/30 heptane/CH2Cl2). The head fractions were pooled to give 12 g (yield: 57%) of benzyl 2-hydroxy-4-(2-methylallyloxy)benzoate in the form of a colourless oil.

Workup

  1. custombrought to 70° C.
  2. filtrationthe salts are filtered off
  3. washThe salts were washed with DMF
  4. customthe solvent was evaporated off
  5. customA brown oil was obtained which
  6. customwas purified on silica (eluent: 70/30 heptane/CH2Cl2)

Sources & evidence

ORD record
ord-71bd019167044c588c71b820d44cdbe3
Source dataset
uspto-grants-1998_05
Patent number
US05756485

Linked notes

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