Potassium bisulfate → HCID 57771482, compound

HRID 2070588Notes

Reaction equation

HRID 2070588 reaction equation
C[C@@H](N)C1C=CC=CC=1.[OH:10][C:11]1[CH:16]=[CH:15][C:14]([C@H:17]([C:22]#[C:23][CH3:24])[CH2:18][C:19]([OH:21])=[O:20])=[CH:13][CH:12]=1.S([O-])(O)(=O)=O.[K+]>C(OCC)(=O)C>[OH:10][C:11]1[CH:12]=[CH:13][C:14]([C@H:17]([C:22]#[C:23][CH3:24])[CH2:18][C:19]([OH:21])=[O:20])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 516920Potassium bisulfateHCID 86632264HCID 86632264, compound

Product 1

HCID 57771482HCID 57771482, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(R)-3-(4-hydroxyphenyl)-hex-4-ynoic acid (R)-α-methylbenzylamine salt (40 g) obtained in Step 1 was suspended in ethyl acetate (300 mL)-saturated aqueous potassium hydrogen sulfate solution (30 mL). The suspension was vigorously stirred until it became a solution, followed by extraction of the reaction mixture with ethyl acetate twice. The organic layer was washed successively with water and saturated brine, dried and concentrated to give (R)-3-(4-hydroxyphenyl)-hex-4-ynoic acid (25 g).

Workup

  1. extractionfollowed by extraction of the reaction mixture with ethyl acetate twice
  2. washThe organic layer was washed successively with water and saturated brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-23d6572eaa604596b7ad01e51149f280
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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