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Water → HCID 86629543, compound

HRID 1666299
Notes
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Reaction equation

HRID 1666299 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:8]=[C:9]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[CH:10]([OH:15])[C:11]([O:13][CH3:14])=[O:12].C(N(CC)CC)C.O>ClCCl>[Cl:6][C:7]1[CH:8]=[C:9]([CH:10]([O:15][S:2]([CH3:1])(=[O:4])=[O:3])[C:11]([O:13][CH3:14])=[O:12])[CH:16]=[C:17]([Cl:19])[CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 56978223(3,5-Dichloro-phenyl)-hydroxy-acetic acid methyl ester

Product 1

HCID 86629543HCID 86629543, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

Methanesulfonyl chloride (9.3 g) was added at 0° C. to a solution of methyl 3,5-dichloromandelate (19.0 g) and triethylamine (8.2 g) in dichloromethane (150 ml). After the addition, the mixture was stirred at room temperature for 3 hours, after which water (150 ml) was carefully added. The organic phase was separated, dried and concentrated to dryness, giving methyl 2-(3,5-dichlorophenyl)-2-mesyloxy-acetate (23.6 g) as an oil.

Workup

  1. additionAfter the addition
  2. customThe organic phase was separated
  3. customdried
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-4f8f5d69a3ae4440ae955a08aa4a95d3
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08044067B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes