Water → HCID 86241471, compound

HRID 2076607Notes

Reaction equation

HRID 2076607 reaction equation
[CH2:1](O)[CH:2]=[CH2:3].S(=O)(=O)(O)O.[Cl:10][C:11]1[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:12]=1[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]([OH:27])=[O:26])=[CH:20][CH:19]=1.O>C1C=CC=CC=1>[Cl:10][C:11]1[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:12]=1[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]([O:27][CH2:3][CH:2]=[CH2:1])=[O:26])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 7858Allyl AlcoholHCID 67119167HCID 67119167, compound

Product 1

HCID 86241471HCID 86241471, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

After allyl alcohol (7.0 ml, 103 mmol) and concentrated sulfuric acid (0.1 ml) were successively added to a solution of (2′-chloro-4′-hydroxy-1,1′-biphenyl-4-yl)acetic acid (1.93 g, 7.35 mmol) obtained in Example (13-1) in benzene (30 ml), the mixture was heated under reflux for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate (twice). The organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=90/10-65/35) to give allyl (2′-chloro-4′-hydroxy-1,1′-biphenyl-4-yl)acetate as a white powder (1.97 g, yield: 899.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. extractionextracted with ethyl acetate (twice)
  4. washThe organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe residue obtained
  7. customby removing the solvent under reduced pressure
  8. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=90/10-65/35)

Sources & evidence

ORD record
ord-1934b1e5dce84e9aaf5c1b3d23136e76
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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