4-Hydroxybenzoic Acid → Benzoic acid, 4-(phenylmethoxy)-, phenylmethyl ester

HRID 1459133

반응식

HRID 1459133 반응식
[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:18](N(C)C)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.OC1C=CC(C(O)=O)=CC=1.ClCC1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([O:15][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:14])=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

8

반응물 6

HCID 1354-Hydroxybenzoic AcidHCID 5238Sodium IodideHCID 7503Benzyl ChlorideHCID 7681N,N-DimethylbenzylamineHCID 11430Potassium CarbonateHCID 738804-(Benzyloxy)benzoic acid

생성물 1

HCID 91863Benzoic acid, 4-(phenylmethoxy)-, phenylmethyl ester수율 76%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

4-(Phenylmethoxy)benzoic acid. In a modification of the literature method [E. L. Elied, R. P. Anderson, Reactions of esters with targeting amines. I. Benzyl esters from methyl esters and benzyldimethylamine, J. Am. Chem. Soc., 1952, 74, 547-549] a mixture of 4-hydroxybenzoic acid (27.6 g, 200 mmol), chloromethylbenzene (57.0 g, 450 mmol), potassium carbonate (50 g) and sodium iodide (25 g) was boiled under reflux in acetonitrile (500 mL) for 16 h. The suspension was filtered and the solvent was evaporated from the filtrate under reduced pressure. The residue was recrystallised from ethanol to give phenylmethyl 4-(phenylmethoxy)benzoate (48.8 g, 76%). Phenylmethyl 4-(phenylmethoxy)benzoate (48.8 g, 150 mmol) was boiled under reflux with aqueous sodium hydroxide (2M; 250 mL) and ethanol (250 mL) for 4 h. The ethanol was evaporated under reduced pressure. Water (1000 mL) was added. The white solid was collected by filtration, warmed to 65° C. with aqueous sulphuric acid (2M; 300 mL) for 1 h and extracted with warm ethyl acetate. The ethyl acetate solution was dried with anhydrous magnesium sulphate and the solvent was evaporated under reduced pressure to give 4-(phenylmethoxy)benzoic acid (27.15 g, 80%). The filtrate was washed twice with diethyl ether, acidified by addition of sulphuric acid (2M) and extracted with diethyl ether. Evaporation of the diethyl ether gave a further portion of 4-(phenylmethoxy)benzoic acid (6.0 g, 18%). The total yield was 98%.

후처리

  1. filtrationThe suspension was filtered
  2. customthe solvent was evaporated from the filtrate under reduced pressure
  3. customThe residue was recrystallised from ethanol

출처 및 근거

ORD 기록
ord-efd3215566064eaf904a5aed70e508b5
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05853713

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