Hydrochloric Acid → HCID 20286765, compound

HRID 127297Notes

Reaction equation

HRID 127297 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]([CH3:20])([CH3:19])[CH:8](O)[CH2:9][C:10](=[O:17])[CH2:11][C:12]([O:14]CC)=[O:13])=[CH:4][CH:3]=1.ClC1C=CC(OC(C)(C)C=O)=CC=1.[BH4-].[Na+].[OH-].[K+].Cl>C(O)C.CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]([CH:8]2[O:14][C:12](=[O:13])[CH2:11][CH:10]([OH:17])[CH2:9]2)([CH3:19])[CH3:20])=[CH:21][CH:22]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 4311764Sodium borohydrideHCID 12851236HCID 12851236, compoundHCID 20286774HCID 20286774, compound

Product 1

HCID 20286765HCID 20286765, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

10 g (0.0354 mole) of ethyl 6-(p-chlorophenoxy)-6-methyl-5-hydroxy-3-oxoheptanoate [prepared from 2-(p-chlorophenoxy)-2-methylpropanal according to the procedure of step (a) of Example 1] were reduced with 0.8 g (0.021 mole) of sodium borohydride in 100 ml of ethanol, with ice-cooling and stirring. The residue obtained from the reaction mixture by the procedure described in Example 1 was dissolved, without purification, in 50 ml of acetone, and then 100 ml of a 15% w/w aqueous solution of potassium hydroxide was added. The mixture was then stirred at room temperature for 20 hours, after which it was acidified with hydrochloric acid and extracted three times, each time with 100 ml of ethyl acetate. The combined extracts were dried over anhydrous sodium sulphate and then the solvent was evaporated off under reduced pressure. The residue was adsorbed on a silica gel chromatography column and fractions eluted with a 1:5 by volume mixture of benzene and ethyl acetate were evaporated to dryness to give 2.6 g (yield 30%) of the desired Compound No. 4. This was recrystallized to give colourless crystals melting at 72°-76° C.

Workup

  1. temperaturecooling
  2. customThe residue obtained from the reaction mixture by the procedure
  3. stirringThe mixture was then stirred at room temperature for 20 hours
  4. extractionextracted three times
  5. dry with materialThe combined extracts were dried over anhydrous sodium sulphate
  6. customthe solvent was evaporated off under reduced pressure
  7. washeluted with a 1:5 by volume mixture of benzene and ethyl acetate
  8. customwere evaporated to dryness

Sources & evidence

ORD record
ord-7bacbb3577154d8f85d6569bbb2ca523
Source dataset
uspto-grants-1981_03
Patent number
US04255444

Reaction notes

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