Benzoin → HCID 70215516, compound

HRID 2271234Notes

Reaction equation

HRID 2271234 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[C:21]1([C:27]([CH:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)O)=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C)C=O.ClCCl>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:27](=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8400BenzoinHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 5622014-(Benzyloxy)butanoic acid

Product 1

HCID 70215516HCID 70215516, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

1.5 g of 4-benzyloxybutanoic acid are dissolved in 10 ml of anhydrous toluene in a reactor under a nitrogen atmosphere. 1.45 ml of 98% oxalyl chloride (2.1 eq.) and 4 drops of dimethylformamide, in order to catalyze the reaction, are subsequently added. The reaction mixture is left to react at room temperature for 1 hour. The solution is concentrated to dryness under vacuum. The orange oil obtained is dissolved in dichloromethane and then introduced dropwise into a reactor, placed under a nitrogen atmosphere, comprising a solution of 1.18 g (0.7 eq.) of benzoin and 1.58 g (2 eq.) of triethylamine in dichloromethane. An immediate evolution of gas is recorded. The reaction mixture is left stirring for 3 hours at room temperature. The reaction mixture is washed 3 times with water, dried over anhydrous sodium sulphate, filtered and finally brought to dryness. The esterified product is then isolated on a silica column (elutent:dichloromethane).

Workup

  1. customthe reaction
  2. additionare subsequently added
  3. waitThe reaction mixture is left
  4. customto react at room temperature for 1 hour
  5. concentrationThe solution is concentrated to dryness under vacuum
  6. customThe orange oil obtained
  7. additionintroduced dropwise into a reactor
  8. waitThe reaction mixture is left
  9. washThe reaction mixture is washed 3 times with water
  10. dry with materialdried over anhydrous sodium sulphate
  11. filtrationfiltered
  12. customThe esterified product is then isolated on a silica column (elutent:dichloromethane)

Sources & evidence

ORD record
ord-10dc0401f50f49d5bd67886eebee1a0a
Source dataset
uspto-grants-2001_12
Patent number
US06333414B1

Reaction notes

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