Citric Acid → HCID 54470355, compound

HRID 253739Notes

Reaction equation

HRID 253739 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[CH2:6][OH:7].[Li]CCCC.[B:18](OC)([O:21]C)[O:19]C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.O>[CH3:12][O:11][C:9]1[CH:8]=[C:5]([CH2:6][OH:7])[CH:4]=[C:3]([O:2][CH3:1])[C:10]=1[B:18]([OH:21])[OH:19]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 8470Trimethyl borateHCID 697183,5-Dimethoxybenzyl alcoholHCID 178418339Butyllithium

Product 1

HCID 54470355HCID 54470355, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,5-dimethoxybenzyl alcohol (80 g) in THF (1900 ml) was added n-BuLi (1.6 M in n-hexane, 750 ml) portionwise at −50° C. for 0.5 hour under argon. The mixture was warmed up to room temperature for 2 hours and cooled again to −60° C. To the mixture was added (MeO)3B (200 ml). The resulting mixture was warmed to room temperature and stirred over night. To the reaction mixture was added a solution of citric acid (300 g) in H2O (1200 ml) portionwise at 0° C. The aqueous layer was separated, saturated with NaCl and extracted with AcOEt. The combined AcOEt extract was dried (Na2SO4) and evaporated. The crystalline residue was triturated with AcOEt and collected by filtration to yield the title compound (75.1 g). mp. 92-98° C.; IR (Nujol) 3460, 3408, 3218, 1613, 1578, 1288, 1231, 1123, 1055, 960, 779 cm−1; MS (APCI) m/z 230 (M+NH4).

Workup

  1. temperaturecooled again to −60° C
  2. temperatureThe resulting mixture was warmed to room temperature
  3. customThe aqueous layer was separated, saturated with NaCl
  4. extractionextracted with AcOEt
  5. extractionThe combined AcOEt extract
  6. dry with materialwas dried (Na2SO4)
  7. customevaporated
  8. customThe crystalline residue was triturated with AcOEt
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-22ad9b53eb434422a40915d723ccca60
Source dataset
uspto-grants-2011_01
Patent number
US07872151B2

Reaction notes

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