Hydrochloric Acid → (5-Iodo-1,3-phenylene)dimethanol

HRID 1016758Notes

Reaction equation

HRID 1016758 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:13]=[C:12]([I:14])[CH:11]=[C:6]([C:7](OC)=[O:8])[CH:5]=1.[Cl-].[Cl-].[Ca+2].[BH4-].[Na+].Cl>C1COCC1.O>[OH:8][CH2:7][C:6]1[CH:5]=[C:4]([CH2:3][OH:2])[CH:13]=[C:12]([I:14])[CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 2758568Dimethyl 5-iodoisophthalateHCID 4311764Sodium borohydrideHCID 5284359Calcium Chloride

Product 1

HCID 22038850(5-Iodo-1,3-phenylene)dimethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of dimethyl-5-iodisophthalate in 800 ml of THF was treated with with 22.2 g of CaCl2. Then, 15.2 g of NaBH4 were added portionwise. The mixture was stirred for one day at room temperature. Then, the mixture was acidified with 250 ml of 3N HCl and diluted with 2 l of H2O. The crude product was isolated by extraction and purified by crystallization from THF/hexane. There were obtained 11.2 g of (3-hydroxymethyl-5-iodo-phenyl)-methanol as white crystals.

Workup

  1. customThe crude product was isolated by extraction
  2. custompurified by crystallization from THF/hexane

Sources & evidence

ORD record
ord-4de35a1aa1f0411ca263e7679dbada30
Source dataset
uspto-grants-2002_11
Patent number
US06476264B2

Reaction notes

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