Sodium Carbonate → Methyl 2-hydroxy-4-(3-phenoxypropoxy)benzoate

HRID 2163722Notes

Reaction equation

HRID 2163722 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CC(=O)CC>[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH2:20][CH2:21][CH2:22][O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 16523Methyl 2,4-DihydroxybenzoateHCID 68522Benzene, (3-bromopropoxy)-

Product 1

HCID 22751303Methyl 2-hydroxy-4-(3-phenoxypropoxy)benzoateYield 64%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

Methyl 2,4-dihydroxybenzoate (33.6g; 0.2 mole) and anhydrous sodium carbonate (34.8g; 0.3 mole) in dry butanone (300 ml) were stirred at reflux during the addition of 1-bromo-3-phenoxypropane (43.0g; 0.2 mole) in butanone (50 ml) and the mixture stirred at reflux for 24 hours. The mixture was cooled and filtered and the filtrate evaporated to a white solid. Recrystallisation from ethanol gave 38.7g (64%) of material of mp 90°-92°, νmax (mull) 1660, 1615, 1598, 1580 cm-1. (Found; C. 67.69; H, 6.22; C17H18O5 requires; C, 67.54; H, 6.00%).

Workup

  1. temperatureat reflux for 24 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customthe filtrate evaporated to a white solid
  5. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-65d6da55a7184498bec3624576d74a71
Source dataset
uspto-grants-1979_01
Patent number
US04136192

Reaction notes

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