Hydrochloric Acid → HCID 178444483, compound

HRID 2309301

Reaction equation

HRID 2309301 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([F:15])[CH:4]=1)[CH3:2].[Cl-].[Cl-].[Cl-].[Al+3].[CH2:20]([C@H:25]1[CH2:30][CH2:29][C@H:28]([CH2:31][C:32](Cl)=[O:33])[CH2:27][CH2:26]1)[CH2:21][CH2:22][CH2:23][CH3:24].Cl>ClCCl>[CH2:20]([C@H:25]1[CH2:26][CH2:27][C@H:28]([CH2:31][C:32]([C:12]2[CH:11]=[CH:10][C:9]([C:6]3[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][C:5]=3[F:15])=[CH:14][CH:13]=2)=[O:33])[CH2:29][CH2:30]1)[CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14903264-Ethyl-2-fluoro-1,1'-biphenylHCID 6451240Aluminum(III) ChlorideHCID 178444488HCID 178444488, compound

Product 1

HCID 178444483HCID 178444483, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Ethyl-2-fluorobiphenyl (13.0 gram) was added in one portion to a stirred suspension of aluminium trichloride (9.54 gram) in dichloromethane (30 ml), followed by a solution of trans-4-n-pentylcyclohexyl acetyl chloride (15 gram) in dichloromethane (30 ml), added dropwise over 30 minutes. After stirring at room temperature for 31/2 hours, the reaction mixture was poured onto ice (250 gram) and hydrochloric acid (25 ml) and the product was extracted with 350 ml and 250 ml portions of petroleum ether (boiling point 60°-80° C.). The combined extracts were washed with water (150 ml), dried over anhydrous sodium sulphate and evaporated to dryness. The residue (26.8 gram) was crystallised from industrial methylated spirits at 0° C. to give 13.2 gram (51.5% yield) 4-(trans-4-n-pentylcyclohexylacetyl)-2'-fluoro-4'-ethylbiphenyl, melting point 72°-73° C.

Workup

  1. additionadded dropwise over 30 minutes
  2. extractionthe product was extracted with 350 ml and 250 ml portions of petroleum ether (boiling point 60°-80° C.)
  3. washThe combined extracts were washed with water (150 ml)
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated to dryness
  6. customThe residue (26.8 gram) was crystallised from industrial methylated spirits at 0° C.

Sources & evidence

ORD record
ord-a48c5a2205d64bc589a453973ad18110
Source dataset
uspto-grants-1987_09
Patent number
US04695131

Linked notes

Loading…