Hydrochloric Acid → HCID 22718798, compound

HRID 1582684Notes

Reaction equation

HRID 1582684 reaction equation
[CH:1]1([C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.II.[CH2:20]([O:22][C:23](=[O:26])[CH2:24]Br)[CH3:21].Cl>C1C=CC=CC=1.[Zn]>[OH:17][C:15]([C:12]1[CH:11]=[CH:10][C:9]([CH:1]2[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:14][CH:13]=1)([CH3:16])[CH2:24][C:23]([O:22][CH2:20][CH3:21])=[O:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 7748Ethyl bromoacetateHCID 22718805HCID 22718805, compound

Product 1

HCID 22718798HCID 22718798, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 241BenzeneSolvent2×

Procedure

To a refluxing mixture of 4′-cyclooctylacetophenone (30 g), I2 (5 mg) and Zn (17.2 g) in benzene (300 ml) was added ethylbromoacetate (18 ml) dropwise during 30 minutes. The mixture was refluxed for 2 h and then cooled to room temperature. It was acidified with 10% HCl (200 ml), benzene layer was separated out. The organic layer was washed with water, dried (Na2SO4) and concentrated. The crude product was purified by column chromatography on silica gel to give 39.4 g (95% yield) of ethyl 3-hydroxy-3-(4′-cyclooctylphenyl)-butanoate (2d, formula 2, R=cyclooctyl) as viscous oil.

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customwas separated out
  3. washThe organic layer was washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-081b6a2b500149c3825c3cc4b0051305
Source dataset
uspto-grants-2004_05
Patent number
US06737438B2

Reaction notes

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