Sodium Chloride → Phenoxyacetyl 1-methyl-1-propyl Carbonate

HRID 398262Notes

Reaction equation

HRID 398262 reaction equation
[Na+].[Cl-].[O:3]([CH2:10][C:11]([OH:13])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+].Cl[C:17]([O:19][CH:20]([CH2:22][CH3:23])[CH3:21])=[O:18]>C(OCC)C>[C:17](=[O:18])([O:19][CH:20]([CH3:21])[CH2:22][CH3:23])[O:12][C:11](=[O:13])[CH2:10][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 19188Phenoxyacetic AcidHCID 11829505sec-Butyl chloroformate

Product 1

HCID 86591391Phenoxyacetyl 1-methyl-1-propyl CarbonateYield 81%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
7.5 °C

Procedure

To a well-stirred reaction vessel equipped with a thermometer and a pH electrode were added 100 ml of diethyl ether, 40 ml of a 25 wt % aqueous NaCl solution, and 0.4 g of Arquad CB50. After cooling the reaction mixture to 5-10° C., 0.066 mole of phenoxy acetic acid was added. The pH was adjusted to a value between 6 and 7 using a 25 wt % aqueous NaOH solution. Then, 0.066 mole of sec-butyl chloroformate was dosed within 5 min at 5-10° C. During this time and a post-reaction time of 40 min at 5-10° C. the pH was kept at 6-7. The reaction mixture was allowed to separate. After removal of the diethyl ether, 15 g of phenoxyacetyl 1-methyl-1-propyl carbonate having a content of 90% were obtained in a yield of 81%.

Workup

  1. customTo a well-stirred reaction vessel
  2. customequipped with a thermometer
  3. customa post-reaction time of 40 min
  4. customat 5-10° C.
  5. customto separate
  6. customAfter removal of the diethyl ether, 15 g of phenoxyacetyl 1-methyl-1-propyl carbonate having a content of 90%
  7. customwere obtained in a yield of 81%

Sources & evidence

ORD record
ord-dd03fa82b1c9421d9b6ba76dfa094d55
Source dataset
uspto-grants-2003_08
Patent number
US06610880B1

Reaction notes

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