4-Chlorophenol → HCID 14390986, compound

HRID 1381749Notes

Reaction equation

HRID 1381749 reaction equation
[C:1]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])(=[O:5])[C@@H:2]([CH3:4])[OH:3].[Cl:11][C:12]1[CH:17]=[CH:16][C:15](O)=[CH:14][CH:13]=1.C1(OP(OC2C=CC=CC=2)OC2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1.CCOCC>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([O:3][C@@H:2]([CH3:4])[C:1]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 46844-ChlorophenolHCID 7540Triphenyl phosphiteHCID 5462977Diethyl azodicarboxylateHCID 10953655tert-butyl (2R)-2-hydroxypropanoate

Product 1

HCID 14390986HCID 14390986, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of known tert-butyl D-(-)-lactate (292 mg), 4-chlorophenol (197 μl) and triphenylphosphite (343 μl) in dry tetrahydrofuran (16 ml) on an ice bath, diethylazodicarboxylate (315 μl) was added dropwise over about 5 minutes. After the addition, the ice bath was removed and the mixture was further stirred at room temperature for 3 hours. The reaction mixture was evaporated with a rotary evaporator (water bath temperature 25° C.). The residue thus obtained was dissolved in ether (20 ml) and the ethereal solution was washed with water. Ether was evaporated. The residue obtained was then purified by silica gel chromatography [silica gel 55 g, eluant:ethyl acetate-hexane (1:10)] to give tert-butyl (2S)-(-)-2-(4'-chlorophenoxy)propionate (330 mg).

Workup

  1. additionAfter the addition
  2. customthe ice bath was removed
  3. customThe reaction mixture was evaporated with a rotary evaporator (water bath temperature 25° C.)
  4. customThe residue thus obtained
  5. washthe ethereal solution was washed with water
  6. customEther was evaporated
  7. customThe residue obtained
  8. customwas then purified by silica gel chromatography [silica gel 55 g, eluant:ethyl acetate-hexane (1:10)]

Sources & evidence

ORD record
ord-dd8978e30e7143e68bad6163ada223c5
Source dataset
uspto-grants-1989_02
Patent number
US04803301

Reaction notes

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