Hydrogen Bromide → NSC12770

HRID 2292102Notes

Reaction equation

HRID 2292102 reaction equation
[C:1]([OH:11])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:12]1([SH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Br>C(O)(=O)C.O>[C:4]1([CH:3]([S:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:2][C:1]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 7969ThiophenolHCID 87842-Propenoic acid, 3-phenyl-

Product 1

HCID 224379NSC12770Yield 70.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Cinnamic acid (30.0 g.), benzenethiol (24.0 g.) and 45% w/v hydrogen bromide in acetic acid (21.5 ml) were heated together at 100° for 7 hrs. The reaction mixture was diluted with water and steam distilled to remove unchanged thiol. The hot aqueous layer was decanted from the oily product, which was recrystallised from 60°-80° petrleum ether to give 3-phenyl-3-(phenylthio)propionic acid (36.7 g) m.pt. 85°-90°. A sample recrystallised again from 60°-80° petroleum ether had m.pt. 88°-90°.

Workup

  1. temperaturewere heated together at 100° for 7 hrs
  2. distillationdistilled
  3. customto remove unchanged thiol
  4. customThe hot aqueous layer was decanted from the oily product, which
  5. customwas recrystallised from 60°-80° petrleum ether

Sources & evidence

ORD record
ord-326a3a402dbc407aa008b7131aa46a1e
Source dataset
uspto-grants-1989_01
Patent number
US04801593

Reaction notes

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