Water → HCID 53876563, compound

HRID 1090178Notes

Reaction equation

HRID 1090178 reaction equation
[OH:1][CH2:2][CH:3]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[C:4]([O:6][CH3:7])=[O:5].[CH3:15][S:16](Cl)(=[O:18])=[O:17].C(N(CC)CC)C.O>C(OCC)C>[CH3:15][S:16]([O:1][CH2:2][CH:3]([C:8]1[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=1)[C:4]([O:6][CH3:7])=[O:5])(=[O:18])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19914733Methyl 2-(4-chlorophenyl)-3-hydroxypropanoate

Product 1

HCID 53876563HCID 53876563, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 5 g of methyl α-(hydroxymethyl)-4-chlorophenylacetate and 3.5 g of methanesulphonyl chloride in 30 ml of anhydrous diethyl ether, cooled at 0° C., a solution of 2.6 g of triethylamine in 10 ml of anhydrous diethyl ether is added dropwise. The temperature is allowed to rise again to room temperature, the reaction mixture is poured into water and is extracted with diethyl ether. The ether solution, washed with water, and dried over Na2SO4, is concentrated under vacuum, to yield 7.2 g of raw product. By crystallization thereof from 5 ml of ethanol, 5.4 g of a white solid product (m.p. 77°-8° C.) is obtained, having the structure indicated in the title of this example.

Workup

  1. customto rise again to room temperature
  2. extractionis extracted with diethyl ether
  3. washThe ether solution, washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationis concentrated under vacuum
  6. customto yield 7.2 g of raw product
  7. customBy crystallization

Sources & evidence

ORD record
ord-e50120bcb4e64c6aa9423343591d018b
Source dataset
uspto-grants-1992_01
Patent number
US05081141

Reaction notes

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