Water → HCID 18787443, compound

HRID 1602448Notes

Reaction equation

HRID 1602448 reaction equation
[CH3:1][C:2]([CH2:4]Cl)=[CH2:3].[OH:6][C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11].C(=O)([O-])[O-].[K+].[K+].O>C1COCC1.CN(C=O)C>[CH2:13]([O:12][C:10](=[O:11])[C:9]1[CH:15]=[CH:16][CH:17]=[C:7]([O:6][CH:1]=[C:2]([CH3:4])[CH3:3])[CH:8]=1)[CH3:14]

Participants

7

Reactant 4

HCID 962WaterHCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 24522Ethyl 3-hydroxybenzoate

Product 1

HCID 18787443HCID 18787443, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-methyl-3-chloropropene (64.2 g, 710 mmol), ethyl 3-hydroxybenzoate (48.21 g, 590 mmol), and potassium carbonate (122.3 g, 890 mmol) in THF (600 ml) and DMF (600 ml) was heated to reflux for 6 hr. The mixture was poured into water (3 L) and extracted with ethyl acetate three times. The ethyl acetate extracts were combined and washed with water and dried with brine. The ethyl acetate extracts were concentrated in vacuo to a yellow oil that was vacuum distilled to a clear oil (112.9 g, 87%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 hr
  3. extractionextracted with ethyl acetate three times
  4. washwashed with water
  5. dry with materialdried with brine
  6. concentrationThe ethyl acetate extracts were concentrated in vacuo to a yellow oil that
  7. distillationdistilled to a clear oil (112.9 g, 87%)

Sources & evidence

ORD record
ord-af63ab3c932f48f992a6c60ada7ca35c
Source dataset
uspto-grants-1999_11
Patent number
US05981571

Reaction notes

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