Methyl 4-[(3-formyl-4-hydroxyphenoxy)methyl]benzoate → HCID 9903578, compound

HRID 479909Notes

Reaction equation

HRID 479909 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[OH:21])[O:6][CH2:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=1)=[O:2]>CCO.[OH-].[Na+].O>[CH:1]([C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[OH:21])[O:6][CH2:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)=[O:2]

Participants

5

Reactant 1

HCID 9921938Methyl 4-[(3-formyl-4-hydroxyphenoxy)methyl]benzoate

Product 1

HCID 9903578HCID 9903578, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A suspension of compound 40 (0.50 g, 1.75 mmol) in a mixture of EtOH (5 mL) and 1N aq NaOH was stirred at room temperature for 2.5 h to give a light yellow solution. The reaction mixture was diluted with water (50 mL), washed with EtOAc (25 mL) and acidified with conc HCl (˜1 mL). The off-white precipitate that formed was collected, washed with water, and dried under high vacuum to give 0.475 g (100%) of 4-[(3-formyl-4-hydroxyphenoxy)methyl]benzoic acid (isotucaresol; III) as a cream-colored powder: mp 222-224° C. (dec); Rf 0.46 (10% MeOH-EtOAc); 1H NMR (300 MHz, acetone-d6) δ10.62 (br s, 1 H, OH), 10.00 (s, 1H, CHO), 8.06 (d, 2H, J=8 Hz, H-2,6), 7.62 (d, 2H, J=8 Hz, H-3,5), 7.43 (d, 1H, J=3 Hz, H-2′), 7.33 (dd, J=3, 8.9 Hz, H-6′), 6.95 (d, 2H, J=8.9 Hz, H-5′), 2.44 (br s, 1H, OH); 13C NMR (75 MHz, acetone-d6) δ197.2, 167.2, 156.7, 152.6, 143.3, 130.9, 130.6, 128.1, 126.5, 121.6, 119.1, 117.6, 70.7; HRMS calcd. for M+NH4+ 290.1028, found 290.1037; Anal. calcd. for C15H12O5.0.25 H2O: C, 65.09; H, 4.55. Found: C, 65.46; H, 4.56.

Workup

  1. customto give a light yellow solution
  2. washwashed with EtOAc (25 mL)
  3. customThe off-white precipitate that formed
  4. customwas collected
  5. washwashed with water
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-eb0badc2c7534e85a2609e1c18a4608b
Source dataset
uspto-grants-2003_11
Patent number
US06649172B2

Reaction notes

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