Water → HCID 21107097, compound

HRID 1765400Notes

Reaction equation

HRID 1765400 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][OH:12])[C:3]=1[CH:4]=O.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21]C(O)=O)=[CH:17][CH:16]=1.[C:25]([O-])(=[O:27])C.[Na+].O>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([O:27][CH3:25])[CH:7]=[C:6]2[C:3]=1[CH:4]=[C:21]([C:18]1[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=1)[C:11](=[O:12])[O:10]2

Participants

6

Reactant 4

HCID 962WaterHCID 76904-Methoxyphenylacetic AcidHCID 517045Sodium AcetateHCID 21107086HCID 21107086, compound

Product 1

HCID 21107097HCID 21107097, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 2-chloro-6-hydroxymethoxybenzaldehyde (2.85 g), 4-methoxyphenylacetic acid (2.54 g) and sodium acetate (3 g) in acetic anhydride (25 mL) was refluxed for 18 h and cooled. Cold water (200 mL) was added. The solids were filtered, washed with water (three times) and ether-hexane (1:1), and dried under high vacuum to give the title compound (2.92 g). 1H NMR (DMSO-d6): 8.03 (s, 1H), 7.68 (d, 2H, J=8.7 Hz), 6.98 (d, 2H, J=8.7 Hz), 6.94 (d, 1H, J=1.8 Hz), 6.77 (d, 1H, J=1.8 Hz), 3.87 (s, 6H).

Workup

  1. temperaturecooled
  2. filtrationThe solids were filtered
  3. washwashed with water (three times) and ether-hexane (1:1)
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-8c3b2541e4924439b2cd61d18ffee9bc
Source dataset
uspto-grants-2007_06
Patent number
US07226945B2

Reaction notes

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