Thioglycolic Acid → 2-[(2,4-Dichlorophenoxy)methyl]-1,3-oxathiolan-5-one

HRID 461282Notes

Reaction equation

HRID 461282 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[O:4][CH2:5][CH:6]=[O:7].[C:13](O)(=[O:16])[CH2:14][SH:15].B(F)(F)F.CCOCC>CCOCC>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[O:4][CH2:5][CH:6]1[S:15][CH2:14][C:13](=[O:16])[O:7]1

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 8000Boron trifluoride etherateHCID 50929372,4-Dichlorophenoxyacetaldehyde

Product 1

HCID 3273742-[(2,4-Dichlorophenoxy)methyl]-1,3-oxathiolan-5-oneYield 40.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution containing 10.25 g (0.05 mole) of 2,4-dichlorophenoxyacetaldehyde, 5.1 g (0.055 mole) of thioglycolic acid and 15 g (0.15 mole) of boron trifluoride etherate in 250 ml of ether was stirred at ambient temperature for 2 hours, washed with 5% aqueous sodium carbonate, dried, concentrated, and triturated with hexane to give 5.6 g of 2-(2,4-dichlorophenoxymethyl)-1,3-oxathiolan-5-one as an off-white crystalline solid melting at 59°-61°.

Workup

  1. washwashed with 5% aqueous sodium carbonate
  2. customdried
  3. concentrationconcentrated
  4. customtriturated with hexane

Sources & evidence

ORD record
ord-f186c2f50e2540beb4e8f59a20e9f1fe
Source dataset
uspto-grants-1977_12
Patent number
US04062670

Reaction notes

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