Methanol → 1-Phenylethanol

HRID 1033940Notes

Reaction equation

[C:1]([O-])(=O)[CH2:2][CH2:3][C:4]([O-])=O.[C:9](=[O:12])([O-])[O-].[K+].[K+].O.[CH3:16][CH2:17]OCC.[CH3:21]O>>[C:1]1([CH:9]([OH:12])[CH3:21])[CH:17]=[CH:16][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 5

HCID 887Methanol

HCID 962Water

HCID 3283Diethyl Ether

HCID 11430Potassium Carbonate

HCID 160419Succinate

Product 1

HCID 74091-Phenylethanol

Procedure

The acetate R-2a (164 mg; 1.0 mmol) was deacetylated by overnight treatment with potassium carbonate (276 mg; 2.0 mmol; 2 equiv.) in methanol (3 mL). The product R-1a (89 mg; 73%) was isolated by dilution with water (25 mL), extraction with ether (2×10 mL), drying of the extracts (MgSO4), and concentration. All achiral properties of 1a are as reported above. 1H nmr analysis of the MTPA ester using an analogous procedure to that of Dale et al., J. Org. Chem., 1969, 34, 2543, indicated 90% ee for R-1a. [α]D20 +40.3° (c. 1.06, CH3OH).

Workup

dry with materialdrying of the extracts (MgSO4), and concentration

Sources & evidence

ORD record: ord-2f6672c145a94f639719d5d46b63cb2f
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05312950

Reaction notes

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