4-Hydroxybenzaldehyde → 4-[(1R)-2-Hydroxy-1-methylethoxy]benzaldehyde

HRID 714440Notes

Reaction equation

HRID 714440 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Cl[C@@H:11]([CH3:14])[CH2:12][OH:13].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[OH:13][CH2:12][C@@H:11]([CH3:14])[O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 10340Sodium CarbonateHCID 641045(S)-(+)-2-Chloro-1-propanol

Product 1

HCID 866919124-[(1R)-2-Hydroxy-1-methylethoxy]benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

Under argon, 785 mg (6.43 mmol) of 4-hydroxybenzaldehyde and 759 mg (8.04 mmol) of (S)-(+)-2-chloro-1-propanol were initially charged in 15.7 ml of DMF. 2.04 g (19.3 mmol) of sodium carbonate were added, and the mixture was then stirred at 130° C. for 20 h. The reaction mixture was purified by preparative HPLC (Chromasil, water/acetonitrile).

Workup

  1. customThe reaction mixture was purified by preparative HPLC (Chromasil, water/acetonitrile)

Sources & evidence

ORD record
ord-6432292a88c94a6c8658ff6dbbe8af02
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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