Ammonium Chloride → HCID 15491191, compound

HRID 1954690Notes

Reaction equation

HRID 1954690 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[CH3:7].[C:23]1([Mg]Br)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[NH4+].[Cl-]>O1CCCC1.CCOCC>[OH:2][C:3]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:4][CH2:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=1)([C:15]1[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=1)[CH3:7]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 247957Methyl 4,4-bis(4-hydroxyphenyl)pentanoateHCID 178418255HCID 178418255, compound3×

Product 1

HCID 15491191HCID 15491191, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4,4-bis(4-hydroxyphenyl)pentanoic acid methyl ester (4.58 g, 15.3 mmol) in 100 mL of anhydrous tetrahydrofuran was cooled to 0° C. and treated dropwise with phenylmagnesium bromide (10 mL of a 3M solution in ether). Additional tetrahydrofuran (50 mL) was added to the reaction mixture followed by phenylmagnesium bromide (10.4 mL of a 3M solution in ether). The reaction was warmed to room temperature and stirred for 3 hours. The reaction was cooled to 0° C. and treated with phenylmagnesium bromide (10.2 mL of a 3M solution in ether). The reaction mixture was warmed to room temperature and stirred for 18 hours. The reaction mixture was cooled to 0° C. and treated with saturated aqueous NH4Cl solution (100 mL). The organic phase was collected and the aqueous phase was extracted with ethyl acetate (3×100 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated. The residue was purified by chromatography (silica gel, 40% ethyl acetate/hexanes) to give the title compound (6.22 g, 96%) as a white solid.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. temperatureThe reaction mixture was warmed to room temperature
  3. stirringstirred for 18 hours
  4. temperatureThe reaction mixture was cooled to 0° C.
  5. customThe organic phase was collected
  6. extractionthe aqueous phase was extracted with ethyl acetate (3×100 mL)
  7. dry with materialThe combined organic extracts were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by chromatography (silica gel, 40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-bead76a8da0f4a40b7fa0c6b7cceae0c
Source dataset
uspto-grants-2000_09
Patent number
US06124280

Reaction notes

Loading…