Sulfuric Acid → HCID 15662570, compound

HRID 2248186Notes

Reaction equation

HRID 2248186 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:20][C@H:21](CS([O-])(=O)=O)[CH2:22][CH3:23].S(=O)(=O)(O)O>CN(C=O)C.O>[CH3:20][C@@H:21]([O:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])=[CH:12][CH:13]=1)[CH2:22][CH3:23]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 602731Methyl 2-(4-hydroxyphenoxy)acetateHCID 18641929HCID 18641929, compound

Product 1

HCID 15662570HCID 15662570, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A mixture of methyl 4-hydroxyphenoxyacetate (25.50 g, 140.0 mmol) and potassium carbonate (18.67 g, 135.0 mmol) in 70 ml of DMF is heated to 75°, with stirring, for 40 min. The above methanesulfonate (10.66 g, 70.0 mmol) in 5 ml of DMF is added slowly over 5 min. The reaction mixture is allowed to stand at 60° overnight. To the cooled reaction mixture is added ice water, followed by cold sulfuric acid to bring it to pH 4-5. Additional water is added and the mixture is extracted with ether (3X). The combined ether extracts are washed with 1% sulfuric acid/1% potassium dihydrophosphate, with 1% potassium dihydrophosphate (2X), then hexane is added and the organic layer is washed with 10% sodium hydroxide (5X), with water and with brine; dried; filtered and the filtrate evaporated to give methyl (R)-(-)-4-(1-methylpropoxy)phenoxyacetate, [α]D20 -20.67.

Workup

  1. temperatureis heated to 75°
  2. waitto stand at 60° overnight
  3. customTo the cooled reaction mixture
  4. extractionthe mixture is extracted with ether (3X)
  5. washThe combined ether extracts are washed with 1% sulfuric acid/1% potassium dihydrophosphate, with 1% potassium dihydrophosphate (2X)
  6. additionhexane is added
  7. washthe organic layer is washed with 10% sodium hydroxide (5X), with water and with brine
  8. customdried
  9. filtrationfiltered
  10. customthe filtrate evaporated

Sources & evidence

ORD record
ord-336a2385cfbd43e3939d2fad2ac4ffe3
Source dataset
uspto-grants-1991_08
Patent number
US05037991

Reaction notes

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