Sodium Hydroxide → (4,5-Dichloro-1,2-phenylene)dimethanol

HRID 1895568Notes

Reaction equation

HRID 1895568 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[C:8]1[C:9]([Cl:22])=[C:10]([Cl:21])[C:11](C)=[C:12]([C:17](O)=[O:18])[C:13]=1[C:14](O)=[O:15].[OH-].[Na+]>C1COCC1.C(OCC)C>[Cl:21][C:10]1[CH:11]=[C:12]([CH2:17][OH:18])[C:13]([CH2:14][OH:15])=[CH:8][C:9]=1[Cl:22]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86653903Dimethyl 4,5-dichlorobenzene-1,2-dicarboxylic acid

Product 1

HCID 13096434(4,5-Dichloro-1,2-phenylene)dimethanolYield 88%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of LiAlH4 (1.61 g, 42.54 mmol) in dry THF (75 mL) cooled to −78° C., a solution of dimethyl 4,5-dichlorobenzene-1,2-dicarboxylic acid (5.0 g, 21.27 mmol) in dry THF (25 mL) was added dropwise over a period of 1 h. After slow warming of the system to RT over a period of 2 h the mixture was heated at reflux overnight. The heterogeneous mixture was then cooled to 0° C. and sodium hydroxide solution (15%, 100 mL) cooled to 0° C. was very slowly added. This was followed by addition of ice-cold water (100 mL), and the reaction mixture was diluted with diethyl ether (200 mL) and the organic layer was separated, dried over MgSO4. Removal of solvents gave a white solid which was passed through a pad of silica gel to afford pure product in 88% yield (3.85 g). 1H NMR (500 MHz, CDCl3): δ 7.60 (s, 2H), 4.65 (s, 4H), 4.50 (bs, 2H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureThe heterogeneous mixture was then cooled to 0° C.
  4. additionwas very slowly added
  5. customthe organic layer was separated
  6. dry with materialdried over MgSO4
  7. customRemoval of solvents
  8. customgave a white solid which
  9. customto afford pure product in 88% yield (3.85 g)

Sources & evidence

ORD record
ord-7122e6f0b8e7471c810f3a19450aa0dc
Source dataset
uspto-grants-2013_08
Patent number
US08513466B2

Reaction notes

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