Diethanolamine → 2-Chloro-1-phenylethanol

HRID 1374925

Reaction equation

HRID 1374925 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].B(Cl)([C@H]1[C@H](C)C2C(C)(C)C(CC2)C1)[C@H]1[C@H](C)C2C(C)(C)C(CC2)C1.N(CCO)CCO>C1COCC1>[Cl:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4]

Participants

5

Reactant 3

HCID 8113DiethanolamineHCID 107572-ChloroacetophenoneHCID 16212015(-)DIP-Chloride

Product 1

HCID 928982-Chloro-1-phenylethanolYield 209.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Chloroacetophenone (3 g., 19.4 mmol) was treated with (−) DIP-chloride (6.7 g., 20.9 mmol) in anhydrous THF (20 mL) at dry-ice bath temperature and left overnight. The temperature was raised to room temperature and THF was removed in vacuo. The residue was dissolved in ether (100 mL). The diethanolamine (4.58 g., 42.6 mmol) was added and the mixture stirred at room temperature for 5 hrs. The separated solid was filtered and the filtered cake was washed with hexane (40 mL) and ether (30 mL). The combined filtrates were evaporated to dryness to give 6.36 g of crude product. This was purified by silica gel column chromatography using 1% ether and petroleum ether 1.71 g (56%) of the desired product was obtained as an oil.

Workup

  1. customTHF was removed in vacuo
  2. dissolutionThe residue was dissolved in ether (100 mL)
  3. filtrationThe separated solid was filtered
  4. washthe filtered cake was washed with hexane (40 mL) and ether (30 mL)
  5. customThe combined filtrates were evaporated to dryness

Sources & evidence

ORD record
ord-028d41eee10e42e09a00b51b250aaeff
Source dataset
uspto-grants-2007_01
Patent number
US07166625B2

Linked notes

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