Hydrochloric Acid → HCID 9827304, compound

HRID 1107930Notes

Reaction equation

HRID 1107930 reaction equation
C[O:2][C:3](=[O:42])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:16][C:15]([C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:14][C:13]=2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:6][C:5]=1[O:38]C(=O)C.C([O-])([O-])=O.[K+].[K+].[OH-].[Na+].Cl>CO.C1COCC1>[C:24]([C:15]1[CH:16]=[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]([O:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:42])=[O:2])=[C:5]([OH:38])[CH:6]=2)=[C:13]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:14]=1)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 53800633HCID 53800633, compound

Product 1

HCID 9827304HCID 9827304, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

At ambient temperature, to a stirred solution of 4-(5'-benzoyl-[1,1';3',1"]terphenyl-2'-yloxymethyl)-2-acetoxy-benzoic acid methyl ester (0.527 g, 0.946 mmol) in MeOH:THF (1:1,15 mL) was added K2CO3 (0.261 g, 1.89 mmol). After 1 h, to the reaction was added 1N NaOH (5 mL) and the reaction was heated at 100° C. for 4 h. The reaction was cooled to ambient temperature, acidified with 1N HCl and extracted with EtOAc. The organic extracts were dried (Na2SO4) and concentrated. Recrystallization from ether/pet. ether gave 0.261g (55%) of the title compound as a white solid, mp 217-220'C. 1H NMR (DMSO-d6) δ 4.25 (s, 2H), 6.29 (dd, 1H), 6.34 (d, 1H), 7.38-7.48 (m, 6H), 7.53-7.69 (m, 8H), 7.72 (s, 2H), 7.82 (d, 2H). IR (KBr) 3050, 1675, 1620, 1575 and 1210 cm-1. mass spectrum (EI) m/z 500 (M+). Anal. Calcd. for C33H24O5H2O: C,76.43; H,5.05; N,0.00. Found: C,76.75; H,4.82; N,0.03.

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. extractionextracted with EtOAc
  3. dry with materialThe organic extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. customRecrystallization from ether/pet. ether

Sources & evidence

ORD record
ord-7a3e7e4b2a4c4b9bac7d8289c5651788
Source dataset
uspto-grants-2000_05
Patent number
US06063815

Reaction notes

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