Dichloromethane → HCID 12962726, compound

HRID 1065531Notes

Reaction equation

HRID 1065531 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][C:7](=[CH2:11])[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[C:14]([OH:22])(=[S:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(Cl)Cl>C(Cl)(Cl)Cl>[C:14]([S:21][CH2:11][CH:7]([CH2:6][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:13][CH:12]=1)[C:8]([OH:10])=[O:9])(=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 12962755HCID 12962755, compoundHCID 178526132HCID 178526132, compound

Product 1

HCID 12962726HCID 12962726, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2-(p-chlorobenzyl)acrylic acid (3.93 gm., 22 mmoles) and thiobenzoic acid (2.6 ml., 20 mmoles) in 40 ml. of methylene chloride was heated at reflux for 16 hours. The reaction mixture was evaporated to dryness and product crystallized from hexane (4.5 g.). Additional product was obtained by evaporation of the hexane mother liquor and chromatography of the residue (7.1 g.) on 200 g. of silica gel (230-400 mesh) with chloroform as eluant; 1.8 g., m.p. 111°-114° C.

Workup

  1. temperatureat reflux for 16 hours
  2. customThe reaction mixture was evaporated to dryness and product
  3. customcrystallized from hexane (4.5 g.)
  4. customAdditional product was obtained by evaporation of the hexane mother liquor and chromatography of the residue (7.1 g.) on 200 g

Sources & evidence

ORD record
ord-ae477c7470724d7fbf5cacdf58987b83
Source dataset
uspto-grants-1982_05
Patent number
US04329495

Reaction notes

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