Ammonium Chloride → 3,5-Di(hydroxymethyl)phenol

HRID 1051844Notes

Reaction equation

HRID 1051844 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12](OC)=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7](OC)=[O:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>O1CCCC1>[OH:1][C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]([CH2:7][OH:8])[CH:11]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 15194153,5-Di(hydroxymethyl)phenolYield 82.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl 5-hydroxyisophthalate (28 g, 133 mmol, 1 eq.) in 1400 mL of dry tetrahydrofuran (THF) at ice-bath temperature, lithium aluminum hydride (LiAlH4 or LAH, 4 eq.) was slowly added with stirring. The resultant mixture was allowed warm to 40° C., stirred at this temperature for 16 hours, and then was added an ammonium chloride (NH4Cl) aqueous solution to quench the reaction. After stirring for 1.5 hours, the mixture was filtered with celite, washed with THF. Organic volatiles were evaporated and the residue was partitioned between water and EtOAc. The aqueous phase was extracted with EtOAc three times. The combined EtOAc layers were dried over MgSO4 to give product (5-hydroxy-1,3-phenylene)dimethanol (17 g, 82%).

Workup

  1. stirringstirred at this temperature for 16 hours
  2. customto quench
  3. customthe reaction
  4. stirringAfter stirring for 1.5 hours
  5. filtrationthe mixture was filtered with celite
  6. washwashed with THF
  7. customOrganic volatiles were evaporated
  8. customthe residue was partitioned between water and EtOAc
  9. extractionThe aqueous phase was extracted with EtOAc three times
  10. dry with materialThe combined EtOAc layers were dried over MgSO4

Sources & evidence

ORD record
ord-8ab56a45d5df442ab31c34b92e6c53d4
Source dataset
uspto-grants-2016_07
Patent number
US09388193B2

Reaction notes

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