Phenol → Phenyl 2,4-dihydroxybenzoate

HRID 2294675

반응식

HRID 2294675 반응식
[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12]1(O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(C)C=CC=CC=1.S(Cl)(Cl)=O>CN(C)C=O>[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5]

참가 물질

6

반응물 4

HCID 996PhenolHCID 1140TolueneHCID 14912,4-Dihydroxybenzoic AcidHCID 24386Thionyl Chloride

생성물 1

HCID 14523517Phenyl 2,4-dihydroxybenzoate수율 54.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

154.1 g (1.0 mol) of 2,4-dihydroxybenzoic acid, 141.2 g (1.5 mol) of phenol, 500 ml of toluene and 1 ml of dimethylformamide are placed in a 1.5 l sulfonating flask fitted with stirrer, condenser, dropping funnel and gas outlet. 178.5 g (1.5 mol) of thionyl chloride are added dropwise over the course of 2.5 hours at an internal temperature of 100-105 C. The reddish, clear solution is then refluxed overnight (110-115 C.). Toluene and phenol are distilled off in vacuo, the highly viscous residue (271.5 g) is stirred in 300 ml of toluene/cyclohexane (7/3) and the mixture is left overnight to crystallize. The precipitate is filtered off with suction under cold conditions (10 C.) and the solid product is washed with 3×50 ml of toluene/cyclohexane (7/3) and then dried at 80 C. in vacuo, to give 125.5 g (54.4% of theory) of phenyl 2,4-dihydroxybenzoate (m.p. 135-137 C.).

후처리

  1. customfitted with stirrer, condenser
  2. temperatureThe reddish, clear solution is then refluxed overnight (110-115 C.)
  3. distillationToluene and phenol are distilled off in vacuo
  4. customto crystallize
  5. filtrationThe precipitate is filtered off with suction under cold conditions (10 C.)
  6. washthe solid product is washed with 3×50 ml of toluene/cyclohexane (7/3)
  7. customdried at 80 C

출처 및 근거

ORD 기록
ord-eb192bf2bcac41b3b20bf84db45f2a97
출처 데이터셋
uspto-grants-1997_11
특허 번호
US05688995

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