Hydrochloric Acid → HCID 22633138, compound

HRID 2417395Notes

Reaction equation

HRID 2417395 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:14]([O:25][CH3:26])=[CH:13][C:12]=2[CH:27]=[O:28])=[C:7]([O:29][CH3:30])[CH:6]=1)=[O:4].[OH-].[Li+].Cl>C1COCC1.O>[CH2:18]([O:17][C:15]1[C:14]([O:25][CH3:26])=[CH:13][C:12]([CH:27]=[O:28])=[C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=2[O:29][CH3:30])[CH:16]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2×HCID 86590422HCID 86590422, compound

Product 1

HCID 22633138HCID 22633138, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 5′-benzyloxy-2′-formyl-2,4′-dimethoxy-biphenyl-4-carboxylic acid methyl ester (5.7 g, 14 mmol) and Lithium hydroxide (0.6 g, 26 mmol) in THF/water(1:1, 30 mL) was stirred overnight at room temperature. Additional Lithium hydroxide (0.2 g, 8.8 mmol) was added and stirring was continued for another 3 h. The reaction mixture was acidified with 2 M hydrochloric acid (500 mL) to pH=4, extracted with ethyl acetate (2×100 mL) and then dichloromethane (50 mL). The organic phases were combined, washed with saturated aqueous ammonium chloride followed by drying and concentration under reduced pressure. Crystallization of the residue from dichloromethane/hexane provided 5′-benzyloxy-2′-formyl-2,4′-dimethoxy-biphenyl-4-carboxylic acid (3.1 g, 57%).

Workup

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. washwashed with saturated aqueous ammonium chloride
  3. customby drying
  4. concentrationconcentration under reduced pressure
  5. customCrystallization of the residue from dichloromethane/hexane

Sources & evidence

ORD record
ord-a4fb086d1da84964bf93144f2059c610
Source dataset
uspto-grants-2004_11
Patent number
US06825208B2

Reaction notes

Loading…