Ammonium Chloride → HCID 54059133, compound

HRID 2295148Notes

Reaction equation

HRID 2295148 reaction equation
[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:12]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][Cl:26])=[CH:17][CH:16]=2)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:29]([Mg]Cl)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:12]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][Cl:26])=[CH:17][CH:16]=2)([OH:14])[CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21469826HCID 21469826, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 54059133HCID 54059133, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Combine 4-benzyloxy-4'-(4-chlorobutyloxy)benzophenone (3.95 g, 10.0 mmol) and tetrahydrofuran (50 mL). Add a solution benzylmagnesium chloride (6.0 mL, 2M in tetrahydrofuran, 12 mmol). After 1 hour, cool to 0° C. and add a saturated aqueous solution of ammonium chloride and stir for 1 hour to give a solid. Filter the solid and rinse three times with tetrahydrofuran. Combine the filtrate and rinses and separate the layers. Extract the organic layer with a saturated sodium chloride solution. Dry the organic layer over MgSO4, filter, and dry in vacuo to give a 1-(4-benzyloxyphenyl)-1-(4-(4-chlorobutyloxy) phenyl)-2-phenyl ethanol: Rf =0.36 (silica gel, 30% ethyl acetate/hexane).

Workup

  1. customto give a solid
  2. filtrationFilter the solid
  3. washrinse three times with tetrahydrofuran
  4. customseparate the layers
  5. extractionExtract the organic layer with a saturated sodium chloride solution
  6. dry with materialDry the organic layer over MgSO4
  7. filtrationfilter
  8. customdry in vacuo

Sources & evidence

ORD record
ord-a9fe7c8474ae4261891c817c10547236
Source dataset
uspto-grants-1997_11
Patent number
US05691384

Reaction notes

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