Benzyl Alcohol → Benzyl 2-hydroxy-2-methylpropanoate

HRID 2226441Notes

Reaction equation

HRID 2226441 reaction equation
[OH:1][C:2]([CH3:7])([CH3:6])[C:3]([OH:5])=[O:4].Cl.C([O-])(O)=O.[Na+].[CH2:14](O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[OH:1][C:2]([CH3:7])([CH3:6])[C:3]([O:5][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:4]

Participants

5

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 116712-Hydroxyisobutyric acidHCID 516892Sodium Bicarbonate

Product 1

HCID 13908920Benzyl 2-hydroxy-2-methylpropanoate

Procedure

2-Hydroxyisobutyric acid (15 gm) was dissolved in benzyl alcohol (80 mL) at 0° C. and the solution was saturated with HCl gas. This solution was stored at rt overnight and then was poured into sat. NaHCO3 solution. This was extracted twice with CHCl3 and the combined organic extracts were dried (Na2SO4), filtered and evaporated to dryness. The residue so obtained was fractionally distilled and the title compound was obtained as a fraction that boiled at 85°-100° C. at 0.2 mm.

Workup

  1. extractionThis was extracted twice with CHCl3
  2. dry with materialthe combined organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue so obtained
  6. distillationwas fractionally distilled

Sources & evidence

ORD record
ord-f3552d4f416c4429954ca3b912e57189
Source dataset
uspto-grants-1994_09
Patent number
US05348953

Reaction notes

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