Hydrochloric Acid → HCID 66990811, compound

HRID 444628Notes

Reaction equation

HRID 444628 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:16][C:15]=2[O:28][CH3:29])=[CH:7][CH:8]=[C:9]([C:11](=[O:13])[CH3:12])[CH:10]=1)=[O:4].[OH-].[Na+].CO.Cl>O>[C:11]([C:9]1[CH:10]=[C:5]([C:3]([OH:4])=[O:2])[C:6]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:16][C:15]=2[O:28][CH3:29])=[CH:7][CH:8]=1)(=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 66990886HCID 66990886, compound

Product 1

HCID 66990811HCID 66990811, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 4-Acetyl-4′-benzyloxy-2′-methoxybiphenyl-2-carboxylic acid methyl ester 7b (4.06 g, 9.7 mmol) and NaOH (0.773 g, 19.4 mmol) was added methanol (60 mL) and water (60 mL). The reaction was refluxed under Ar for 7 h then cooled to room temperature. After placing in an ice bath, 1 M HCl was added to give a yellow precipitate that was filtered, washed with water and recrystallized from THF/hexanes to give 2.7 g (69%) of 8b as yellow crystals. 1H-NMR (400 MHz, CDCl3) dH 2.68 (4H, s, COCH3), 3.62 (3H, s, OCH3), 5.16 (2H, s, CH2Ph), 6.77 (1H, s, ArH), 7.18 (1H, s, ArH), 7.33-7.52 (5H, m, CH2Ph), 3.90 (3H, s, OCH3), 5.22 (2H, S, CH2Ph), 6.58 (1H, s, ArH), 6.90 (1H, s, ArH), 7.34-7.50 (6H, m, ArH+Ch2Ph), 8.17 (1H, d, ArH), 8.50 (1H, s, ArH),

Workup

  1. temperatureThe reaction was refluxed under Ar for 7 h
  2. customAfter placing in an ice bath
  3. customto give a yellow precipitate that
  4. filtrationwas filtered
  5. washwashed with water
  6. customrecrystallized from THF/hexanes

Sources & evidence

ORD record
ord-64d49c6813b044379bed289f5b9607d6
Source dataset
uspto-grants-2013_07
Patent number
US08475776B2

Reaction notes

Loading…