Water → HCID 57801820, compound

HRID 2070589Notes

Reaction equation

HRID 2070589 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:13]#[C:14][CH3:15])[CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.O.[C:22](=O)(O)[O-].[Na+]>CO>[CH3:22][O:11][C:10](=[O:12])[CH2:9][C@H:8]([C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[C:13]#[C:14][CH3:15]

Participants

6

Reactant 4

HCID 962Water2×HCID 1118Sulfuric AcidHCID 516892Sodium Bicarbonate2×HCID 57771482HCID 57771482, compound

Product 1

HCID 57801820HCID 57801820, compoundYield 265%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (R)-3-(4-hydroxyphenyl)-hex-4-ynoic acid (25 g) obtained in Step 2 in methanol (125 mL) was added concentrated sulfuric acid (1.25 mL), followed by stirring the mixture at 80° C. for 2.5 hours. After cooling down to room temperature, water (100 mL) and sodium bicarbonate (4.14 g) were added to the reaction mixture, followed by concentration of the mixture. To the reaction mixture were added water and saturated aqueous sodium bicarbonate solution, followed by extraction with ethylacetate. The organic layer was washed with saturated brine, dried and concentrated. The residue was distilled azeotropically with toluene to give (R)-3-(4-hydroxyphenyl)-hex-4-ynoic acid methyl ester (28.5 g).

Workup

  1. temperatureAfter cooling down to room temperature
  2. extractionfollowed by extraction with ethylacetate
  3. washThe organic layer was washed with saturated brine
  4. customdried
  5. concentrationconcentrated
  6. distillationThe residue was distilled azeotropically with toluene

Sources & evidence

ORD record
ord-5164a4c2153e44a7b8e6295218ccf0e4
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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