Hydrochloric Acid → HCID 21450775, compound

HRID 596151Notes

Reaction equation

HRID 596151 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][C:12](=[O:18])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:5][CH:4]=1.CC(O)C.[B-].[Na+].Cl>O>[OH:18][CH:12]([CH2:11][CH2:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[CH2:13][CH2:14][C:15]([OH:17])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 21450776HCID 21450776, compoundHCID 22959485Vertellus

Product 1

HCID 21450775HCID 21450775, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 79 parts of 4-methoxy-γ-oxobenzeneheptanoic acid in 630 parts of 2-propanol at 0°-5° is added, with stirring during one-half hour, 80 parts of sodium tetrahydroborate(1-). Stirring is continued at 0°-5° for 31/2 hours after the addition is complete, at which point the reaction mixture is consecutively diluted with an equal volume of water and acidified with cold 10% hydrochloric acid. The mixture thus obtained is extracted with cold dichloromethane. The dichloromethane extract is washed with water, dried over anhydrous sodium sulfate, and stripped of solvent by vacuum distillation at temperatures less than 40°. The residue is crystallized from a mixture of cold ether and hexane to give γ-hydroxy-4-methoxybenzeneheptanoic acid melting at approximately 67°-68°, and having the formula ##STR7##

Workup

  1. additionis added
  2. stirringStirring
  3. customis continued at 0°-5° for 31
  4. custom2 hours
  5. additionafter the addition
  6. customThe mixture thus obtained
  7. extractionis extracted with cold dichloromethane
  8. extractionThe dichloromethane extract
  9. washis washed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationstripped of solvent by vacuum distillation at temperatures less than 40°
  12. customThe residue is crystallized from a mixture of cold ether and hexane

Sources & evidence

ORD record
ord-e3ee10a9f89c4520b9a28c0fb3d67bd3
Source dataset
uspto-grants-1977_03
Patent number
US04010169

Reaction notes

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