Potassium Carbonate → HCID 71113254, compound

HRID 332702Notes

Reaction equation

HRID 332702 reaction equation
[OH:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][CH2:21][CH:22]1[O:26][CH2:25][CH2:24][O:23]1>CN(C=O)C.C(OCC)(=O)C>[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH2:19][CH2:20][CH2:21][CH:22]2[O:26][CH2:25][CH2:24][O:23]2)=[O:8])=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 763604-(Hydroxymethyl)benzoic acidHCID 3577832-(3-bromopropyl)-1,3-dioxolane

Product 1

HCID 71113254HCID 71113254, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 4-hydroxymethylbenzoic acid (3.33 g, 21.9 mmol) in DMF (100 mL), was added potassium carbonate (5.67 g, 41.04 mmol) followed by 2-(3-bromopropyl)-1,3-dioxolane (3.0 g, 19.9 mmol). The resulting mixture was heated at 80° C. for 16 hours. The reaction mixture was diluted with ethyl acetate and washed sequentially with water and twice with brine. The organic phase was dried with anhydrous magnesium sulfate, and filtered, and the filtrate evaporated at reduced pressure. The crude material was purified by silica gel chromatography eluting with 100% iso-hexane to 100% ethyl acetate in iso-hexane to afford the title compound as a colourless oil (2.55 g, 48%).

Workup

  1. washwashed sequentially with water and twice with brine
  2. dry with materialThe organic phase was dried with anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe filtrate evaporated at reduced pressure
  5. customThe crude material was purified by silica gel chromatography
  6. washeluting with 100% iso-hexane to 100% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-0f406d5fed30480a8d965ce4291dda68
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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