Thionyl Chloride → HCID 54421434, compound

HRID 1109954Notes

Reaction equation

HRID 1109954 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=O)C.S(Cl)(Cl)=O.[CH3:24][C@@H:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26]O>>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([O:19][CH2:24][C@@H:25]([CH3:26])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:18])=[CH:15][CH:16]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 6118364'-Acetoxy-biphenyl-4-carboxylic acidHCID 11435018116013-69-5

Product 1

HCID 54421434HCID 54421434, compound

Procedure

4'-Acetoxybiphenyl-4-carboxylic acid (5.80 g) was converted to an acid chloride using thionyl chloride, and the acid chloride was reacted with (S)-2-methyloctanol. The reaction mixture was extracted with diethyl ether, and the ethereal layer was thoroughly dried. Benzylamine was added thereto in small portions at room temperature. Hydrochloric acid was further added thereto, and the mixture was washed with water. The solvent was removed from the reaction mixture by distillation, and the resulting crude product was decolored by passing through a silica gel column (solvent: n-hexane-ethyl acetate mixture) and recrystallized from n-hexane to obtain 6.2 g of (S)-2-methyloctyl 4'-hydroxybiphenyl-4-carboxylate as white crystals having a melting point of 89° C.

Workup

  1. extractionThe reaction mixture was extracted with diethyl ether
  2. customthe ethereal layer was thoroughly dried
  3. additionBenzylamine was added
  4. customat room temperature
  5. additionHydrochloric acid was further added
  6. washthe mixture was washed with water
  7. customThe solvent was removed from the reaction mixture by distillation
  8. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-5fa92c9b6fb547b3a0e5f9c727a88503
Source dataset
uspto-grants-1994_06
Patent number
US05324451

Reaction notes

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