Water → HCID 18943088, compound

HRID 400278Notes

Reaction equation

HRID 400278 reaction equation
C[O:2][C:3]([C:5]1[C:16]2[O:15][C:14]([CH3:18])([CH3:17])[O:13][C:12]=2[C:11]([C:19]([C:41]2[C:51]3[O:52][C:53]([CH3:56])([CH3:55])[O:54][C:50]=3[C:49]([C:57]([O:59]C)=[O:58])=[C:43]3[O:44][C:45]([CH3:48])([CH3:47])[O:46][C:42]=23)([C:21]2[C:31]3[O:32][C:33]([CH3:36])([CH3:35])[O:34][C:30]=3[C:29]([C:37]([O:39]C)=[O:38])=[C:23]3[O:24][C:25]([CH3:28])([CH3:27])[O:26][C:22]=23)[OH:20])=[C:10]2[C:6]=1[O:7][C:8]([CH3:62])([CH3:61])[O:9]2)=[O:4].[OH-].[Na+].O>CO.CO.O>[C:37]([C:29]1[C:23]2[O:24][C:25]([CH3:27])([CH3:28])[O:26][C:22]=2[C:21]([C:19]([C:11]2[C:12]3[O:13][C:14]([CH3:18])([CH3:17])[O:15][C:16]=3[C:5]([C:3]([OH:4])=[O:2])=[C:6]3[O:7][C:8]([CH3:61])([CH3:62])[O:9][C:10]=23)([C:41]2[C:51]3[O:52][C:53]([CH3:56])([CH3:55])[O:54][C:50]=3[C:49]([C:57]([OH:59])=[O:58])=[C:43]3[O:44][C:45]([CH3:47])([CH3:48])[O:46][C:42]=23)[OH:20])=[C:31]2[C:30]=1[O:34][C:33]([CH3:36])([CH3:35])[O:32]2)([OH:39])=[O:38]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 11828970HCID 11828970, compound2×

Product 1

HCID 18943088HCID 18943088, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

The ester of Example 15, tris(8-methoxycarbonyl-2,2,6,6-tetramethyl-benzo[1,2-d:4,5-d']bis(1,3)dioxole-4-yl)methanol (0.30 g, 0.34 mmol) was dissolved in MeOH (10 mL), and NaOH (0.041 g, 1.02 mmol) dissolved in MeOH/H2O (2.32M NaOH solution) was added until pH reached 7. In total 0.44 mL of the basic solution was used. The MeOH was evaporated in vacuum due to solubility problems and THF (3.5 mL) was added. The reaction mixture cleared with this treatment. After 12 h the reaction mixture was turbid and a precipitate had formed. This precipitate dissolved with the addition of water (10 mL). The THF was evaporated under reduced pressure and water (10 mL) was added and the aqueous phase was extracted with ether (10 mL). The organic phase was separated and the aqueous phase was acidified (pH 3.5) with 2M HCl. A yellow precipitate was formed and the aqueous phase was extracted with ether (3×20 mL) and CH2Cl2 (30 mL). The organic phases were collected, dried (Na2SO4) and the solvent was evaporated to yield the product tris(8-carboxy-2,2,6,6-tetramethyl-benzo[1,2-d:4,5-d']bis(1,3)dioxole-4-yl)methanol as a slightly tanned residue (0.25 g, 87%). The product contained a small impurity (appreciated to about 2% at the same extinction) according to HPLC (C18, ion pair (tetrabutyl-ammonium acetate) chromatography, CH3CN:H2O) with UV (254 nm) detection.

Workup

  1. additionwas added until pH
  2. customThe MeOH was evaporated in vacuum due to solubility problems and THF (3.5 mL)
  3. additionwas added
  4. customturbid and a precipitate had formed
  5. customThe THF was evaporated under reduced pressure and water (10 mL)
  6. additionwas added
  7. extractionthe aqueous phase was extracted with ether (10 mL)
  8. customThe organic phase was separated
  9. customA yellow precipitate was formed
  10. extractionthe aqueous phase was extracted with ether (3×20 mL) and CH2Cl2 (30 mL)
  11. customThe organic phases were collected
  12. dry with materialdried (Na2SO4)
  13. customthe solvent was evaporated

Sources & evidence

ORD record
ord-1e354e44af0b47da9dd6961178c5cdb0
Source dataset
uspto-grants-1998_10
Patent number
US05827501

Reaction notes

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