Carbon Dioxide → 3-Iodobenzyl alcohol

HRID 420415Notes

Reaction equation

HRID 420415 reaction equation
ClC(OCC)=O.[I:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11](O)=[O:12].C(N(CC)CC)C.[BH4-].[Na+].C(=O)=O.Cl>O1CCCC1.O>[I:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[CH2:11][OH:12]

Participants

9

Reactant 6

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 120603-Iodobenzoic acidHCID 4311764Sodium borohydride

Product 1

HCID 423003-Iodobenzyl alcohol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl chloroformate (1.02 g, 11.1 mmol) in dry tetrahydrofuran (5 ml) was added slowly over 10 min to a stirred solution of 3-iodobenzoic acid (1.98 g, 7.98 mmol) and triethylamine (0.500 g, 11.6 mmol) in dry tetrahydrofuran at −8° (ice/salt/water bath). The yellow mixture soon became cloudy. It was shielded from light and stirred at −8° for 0.5 h, after which it was filtered to remove the triethylammonium chloride precipitate. The filtrate was added slowly to a suspension of sodium borohydride (0.795 g, 21.1 mmol) in water (30 ml) in a three necked flask, equipped with a thermometer, and connected to nitrogen, making sure that the temperature of the mixture is kept below 10° during the addition. Gas evolution (carbon dioxide) was observed. After the addition was completed, the mixture was stirred, shielded from light, at room temperature for 22 h under nitrogen. The resultant cloudy mixture was acidified with aqueous hydrochloric acid (10%) to pH˜1. The layers were separated, and the aqueous layer was extracted with ether (×3). The combined ether extract and tetrahydrofuran layer was washed with aqueous sodium hydroxide (×1, 10%) and then with water (×1). Drying with magnesium sulphate, and concentration gave 3-iodobenzyl alcohol (11) a pale yellow oil (1.02 g, 54%).

Workup

  1. filtrationafter which it was filtered
  2. customto remove the triethylammonium chloride precipitate
  3. customequipped with a thermometer
  4. additionis kept below 10° during the addition
  5. additionAfter the addition
  6. stirringthe mixture was stirred
  7. waitshielded from light, at room temperature for 22 h under nitrogen
  8. customThe layers were separated
  9. extractionthe aqueous layer was extracted with ether (×3)
  10. extractionThe combined ether extract
  11. washtetrahydrofuran layer was washed with aqueous sodium hydroxide (×1, 10%)
  12. dry with materialDrying with magnesium sulphate, and concentration

Sources & evidence

ORD record
ord-a5ff4f12944946f39488a8861a9622bd
Source dataset
uspto-grants-2012_01
Patent number
US08097238B2

Reaction notes

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