HCID 10691343, compound → HCID 9842240, compound

HRID 322847Notes

Reaction equation

HRID 322847 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[CH:16]=[CH:15][C:10]=1[C:11]([O:13]C)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCOCC1.[OH-].[Na+]>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)[CH:16]=[CH:15][C:10]=1[C:11]([OH:13])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 10691343HCID 10691343, compound

Product 1

HCID 9842240HCID 9842240, compoundYield 44.2%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 2-benzyloxy-4-(4-chlorobenzyloxy)benzoate (1.88 g) in dioxan (37 mL) and 1M NaOH (12.5 mL) is refluxed for 4 hours. The solution is evaporated, the residue diluted with water, and brought to pH 1 with 2M HCl. The precipitate is extracted with ethyl acetate, washed with water, dried and evaporated. The residue is recrystallized from ethyl acetate to yield 2-benzyloxy-4-(4-chlorobenzyloxy)benzoic acid (0.8 g, 44%) as colourless crystals, m.p. 150-152° C. 1H NMR (DMSO) 5.15 (2H,s), 5.2(2H,s), 6.7(1H,d), 6.8(1H,s), 7.3-7.5(9H,m), 7.7(1H,d).

Workup

  1. customThe solution is evaporated
  2. additionthe residue diluted with water
  3. extractionThe precipitate is extracted with ethyl acetate
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-750612fb644e4043949cf996ac15b9e8
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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