Water → Methyl 3-hydroxy-5-isopropoxybenzoate

HRID 1011681Notes

Reaction equation

HRID 1011681 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].I[CH:20]([CH3:22])[CH3:21].O>CN(C=O)C.C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH:20]([CH3:22])[CH3:21])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 75076Methyl 3,5-Dihydroxybenzoate

Product 1

HCID 23072925Methyl 3-hydroxy-5-isopropoxybenzoate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methyl 3,5-dihydroxybenzoate (0.1 mol) in DMF (180 mL) was added powdered potassium carbonate (0.2 mol) and 2-iodopropane (0.1 mol), and the resulting mixture stirred at ambient temperature for 16 hours. The reaction mixture was poured into water (1000 mL) and the mixture extracted with ether. The extracts were combined and washed sequentially with water (twice) and brine; the solution was dried (MgSO4), filtered and evaporated in vacuo to give the crude product as a pale yellow oil (12.6 g). This was treated with toluene (40 mL) and allowed to stand overnight. The insoluble material (starting phenol) was removed by filtration, and the filtrate evaporated in vacuo. The resulting oil was chromatographed (2×90 g Biotage silica cartridges), eluting with hexane containing ethyl acetate (10% increasing to 15% v/v). The title compound was obtained as an oil (25% yield), which was identical by tlc to a sample prepared by a similar procedure. 1H NMR δ (d6-DMSO): 1.2 (d, 6H), 3.8 (s, 3H), 4.5-4.6 (hept, 1H), 6.55 (m, 1H), 7.85 (m, 1H), 7.95 (m, 1H), 9.8 (s, 1H)

Workup

  1. extractionthe mixture extracted with ether
  2. washwashed sequentially with water (twice) and brine
  3. dry with materialthe solution was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give the crude product as a pale yellow oil (12.6 g)
  7. waitto stand overnight
  8. customThe insoluble material (starting phenol) was removed by filtration
  9. customthe filtrate evaporated in vacuo
  10. customThe resulting oil was chromatographed (2×90 g Biotage silica cartridges)
  11. washeluting with hexane
  12. additioncontaining ethyl acetate (10%
  13. temperatureincreasing to 15% v/v)

Sources & evidence

ORD record
ord-a3fe2c7149f44fa3adb2e16d17ac8f48
Source dataset
uspto-grants-2011_07
Patent number
US07977328B2

Reaction notes

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