Methanol → Methyl 2-(4-benzyloxyphenyl)acetate

HRID 1472970Notes

Reaction equation

HRID 1472970 reaction equation
S(Cl)(Cl)=O.[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:23]O>>[CH3:23][O:21][C:20](=[O:22])[CH2:19][C:16]1[CH:15]=[CH:14][C:13]([O:12][CH2:5][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 810334-Benzyloxyphenylacetic acid

Product 1

HCID 2756645Methyl 2-(4-benzyloxyphenyl)acetate

Conditions

Temperature
7.5 °C

Procedure

Thionyl chloride (60 ml; 0.83 mol) was added drop-wise to a mixture of (4-benzyloxy-phenyl)acetic acid (100 gm; 0.4132 mol) and methanol (300 ml) under constant stirring while maintaining the temperature at 5-10° C. After complete addition, the reaction mixture was stirred for 5-6 hours at room temperature. After completion of the reaction, white crystalline solid was isolated by filtration to yield (4-benzyloxy-phenyl)-acetic acid methyl ester. Yield: 104 g, Efficiency: 98.31%.

Workup

  1. additionAfter complete addition
  2. stirringthe reaction mixture was stirred for 5-6 hours at room temperature
  3. customAfter completion of the reaction
  4. customwhite crystalline solid was isolated by filtration

Sources & evidence

ORD record
ord-9ba121088a254217a6cd6b52763054bc
Source dataset
uspto-grants-2015_04
Patent number
US09012689B2

Reaction notes

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