Ammonium Chloride → HCID 67686974, compound

HRID 2295138Notes

Reaction equation

HRID 2295138 reaction equation
ClCCCCO[C:7]1[CH:20]=[CH:19][C:10]([C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])=[CH:9][CH:8]=1.[CH2:21]([Mg]Cl)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-:30].[NH4+]>O1CCCC1>[Cl:30][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1([C:11]([C:10]2[CH:9]=[CH:8][CH:7]=[CH:20][CH:19]=2)([OH:12])[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH2:18]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21469848HCID 21469848, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 67686974HCID 67686974, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine 4-(4-chlorobutoxy)benzophenone (8.1 kg, 13.47 mol) and tetrahydrofuran (60 L). Add a solution of benzylmagnesium chloride (21 L, 1.67M in tetrahydrofuran, 35 mol) over about 2.5 hours. After 2 hours, cautiously add aqueous saturated ammonium chloride solution (9 L) over about 1 hour and a precipitate forms. Filter the reaction mixture, rinse with tetrahydrofuran, and extract the filtrate with aqueous saturated sodium chloride solution. Evaporate the separated organic layer in vacuo to give 1-(4-chlorobutoxy)phenyl-1,2-diphenyl ethanol.

Workup

  1. filtrationFilter the reaction mixture
  2. washrinse with tetrahydrofuran
  3. extractionextract the filtrate with aqueous saturated sodium chloride solution
  4. customEvaporate the separated organic layer in vacuo

Sources & evidence

ORD record
ord-91a31a4dae1d472f9d0f99c11ae970fa
Source dataset
uspto-grants-1997_11
Patent number
US05691384

Reaction notes

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