Water → 3,4,5-Tris(benzyloxy)benzoic Acid

HRID 1894918Notes

Reaction equation

HRID 1894918 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:12]([O:14]C)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].O>CC(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:18]=1[O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 352181Methyl 3,4,5-Tris(benzyloxy)benzoate

Product 1

HCID 111339693,4,5-Tris(benzyloxy)benzoic Acid

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

To a mixture of methyl 3,4,5-tribenzyloxybenzoate (15) (20.60 g, 45.30 mmol) in 2-propanol (200 mL) was added a solution of potassium hydroxide (3.50 g, 85%, 53.00 mmol) in 2-propanol (25 mL). The mixture was refluxed for 1 h, cooled, and water was added (250 mL). A white precipitate appeared, and the mixture was filtered. Recrystallisation from ethyl acetate afforded the desired compound as white crystals, m.p. 194-195° C. Yield: 17.2 g (86%). 1H NMR (300 MHz, DMSO-d6): δ=5.05 (2H, s), 5.18 (4H, s), 7.24-7.50 (17H, m), 13.4 (1H, s, broad); 13C NMR (75 MHz): δ=70.3, 74.3, 108.3, 126.1, 127.7, 128.0, 128.2, 128.3, 128.5, 136.9, 137.5, 141.0, 152.1, 167.0.

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. temperaturecooled
  3. filtrationthe mixture was filtered
  4. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-9d25e50f35b14b00a05344e16142ed05
Source dataset
uspto-grants-2013_08
Patent number
US08513395B2

Reaction notes

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