Hydrochloric Acid → Methyl (2-hydroxyphenyl)acetate

HRID 581696Notes

Reaction equation

HRID 581696 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].Cl.[CH3:13]O>>[CH3:13][O:10][C:9](=[O:11])[CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[OH:1]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11970(2-Hydroxyphenyl)acetic acid

Product 1

HCID 89719Methyl (2-hydroxyphenyl)acetateYield 95%

Procedure

To a solution of 2-hydroxyphenylacetic acid (20.0 g, 129.7 mmol) in 250 mL of methanol was bubbled at room temperature anhydrous hydrochloric acid for 5 minutes. The reaction was capped and stirred overnight. The reaction was then concentrated under reduced pressure to yield a pale oil (20.5 g, 95%). 1H NMR (300 MHz, DMSO): δ 9.45 (s, 1H), 7.15 (m, 2H), 6.75 (m, 2H), 3.57 (d, 2H), 3.35 (s, 3H).

Workup

  1. customThe reaction was capped
  2. concentrationThe reaction was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-5ab4ba42d63d459eb4d6e48b14cd26ea
Source dataset
uspto-grants-1999_07
Patent number
US05922697

Reaction notes

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