Chloroacetic Acid → (E)-1-(3-phenoxyphenyl)but-1-en-3-yl chloroacetate

HRID 704809Notes

Reaction equation

HRID 704809 reaction equation
[O:1]([C:8]1[CH:9]=[C:10](/[CH:14]=[CH:15]/[CH:16]([OH:18])[CH3:17])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:19][CH2:20][C:21](O)=[O:22].C1CCC(N=C=NC2CCCCC2)CC1.CCOCC>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:19][CH2:20][C:21]([O:18][CH:16]([CH3:17])/[CH:15]=[CH:14]/[C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:9]=1)=[O:22]

Participants

7

Reactant 4

HCID 300Chloroacetic AcidHCID 3283Diethyl EtherHCID 10868DicyclohexylcarbodiimideHCID 20073356HCID 20073356, compound

Product 1

HCID 20073365(E)-1-(3-phenoxyphenyl)but-1-en-3-yl chloroacetateYield 99.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The product from step (b) (12.01 g) and chloroacetic acid (5 g) were taken up in methylene chloride, DCC (15 g) was added, and the mixture stirred for 5 minutes. DMAP (0.5 g) was then added, causing the mixture to boil, and the mixture stirred for 1 hour. Ether (200 ml) was then added, the mixture filtered, and the filtrate washed with satd. aqu. NaHCO3, 2 M aqu. HCl, and satd. aqu. NaCl, dried over MgSO4 and stripped. The residue was taken up in ether/pet.ether (1:1, 100 ml). filtered, and stripped to give the desired product (15.7 g).

Workup

  1. stirringthe mixture stirred for 1 hour
  2. filtrationthe mixture filtered
  3. washthe filtrate washed with satd
  4. dry with materialNaCl, dried over MgSO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-6a1f7a21dc614ed287d4993ce04247c7
Source dataset
uspto-grants-1991_01
Patent number
US04988733

Reaction notes

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