Hydrochloric Acid → 3-Benzyloxy-p-anisic acid

HRID 475547Notes

Reaction equation

HRID 475547 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[C:12]([O:14]C)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C(#N)C.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[C:12]([OH:14])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4171221Methyl 3-(benzyloxy)-4-methoxybenzoate

Product 1

HCID 940573-Benzyloxy-p-anisic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

A 25 g quantity of the methyl 3-benzyloxy-4-methoxybenzoate obtained in Reference Example 2 was dissolved in 100 ml of acetonitrile, and a solution of 11 g of sodium hydroxide in 100 ml of water was added. The mixture was stirred with heating at 40° C. for 5 hours. The reaction mixture was cooled with ice, and concentrated hydrochloric acid was added to give a pH of about 3. The precipitated crystals were collected by filtration and dried under reduced pressure to give 22.1 g of white crystalline 3-benzyloxy-4-methoxybenzoic acid.

Workup

  1. additionwas added
  2. customto give a pH of about 3
  3. filtrationThe precipitated crystals were collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-17ce62fdbbec48db82db95e8ac4a34e0
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

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