Hydrochloric Acid → HCID 67979919, compound

HRID 2040934Notes

Reaction equation

HRID 2040934 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:6][CH:5]=1.[CH:22](OC)=[O:23].Cl>O1CCCC1.C(OCC)(=O)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15](=[CH:22][OH:23])[C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7865Methyl formateHCID 24758Sodium hydrideHCID 67333310HCID 67333310, compound

Product 1

HCID 67979919HCID 67979919, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
2.5 °C

Procedure

12.92 g (0.32 mol) of a 60% sodium hydride dispersion in mineral oil were suspended in 400 mL of tetrahydrofuran. After cooling to 0-5° C., a solution containing 45 g (0.16 mol) of methyl 2-(4-chlorophenoxy)phenylacetate (compound VIIIb), as obtained in Example 6, in 300 mL of tetrahydrofuran, was added dropwise while keeping the temperature below 10° C. After the addition, the reaction mixture was stirred at 0-5° C. for 30 minutes. Then, 36.3 g (0.60 mol) of methyl formate were added dropwise, while keeping the temperature below 10° C. After the addition, the reaction mixture was stirred at room temperature overnight. 50 mL of 2 M aqueous hydrochloric acid were added. Then, 200 mL of ethyl acetate were added and the phases were decanted. The organic phase was extracted and washed with 200 mL of water and 200 mL of saturated sodium chloride. The organic phase was concentrated to dryness under reduced pressure, to obtain 40 g of methyl 2-[2-(4-chlorophenoxy)phenyl]-3-hydroxyacrylate (compound IXb) after chromatographic purification. Yield: 80.7%.

Workup

  1. additionwas added dropwise
  2. customthe temperature below 10° C
  3. additionAfter the addition
  4. customthe temperature below 10° C
  5. additionAfter the addition
  6. stirringthe reaction mixture was stirred at room temperature overnight
  7. customthe phases were decanted
  8. extractionThe organic phase was extracted
  9. washwashed with 200 mL of water and 200 mL of saturated sodium chloride
  10. concentrationThe organic phase was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1c861bbc58754920afb7e4eff2596261
Source dataset
uspto-grants-2013_11
Patent number
US08580972B2

Reaction notes

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