Hydrochloric Acid → Methyl (2-(hydroxymethyl)-3-methylphenyl)carbamate

HRID 2073794Notes

Reaction equation

HRID 2073794 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][C:7]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:8]=1[CH2:9][OH:10].N1C=CC=CC=1.Cl>C(Cl)Cl>[CH3:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:7]([NH:6][C:2]([O:4][CH3:5])=[O:3])[C:8]=1[CH2:9][OH:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6586Methyl chloroformateHCID 15339417(2-Amino-6-methylphenyl)methanol

Product 1

HCID 14368454Methyl (2-(hydroxymethyl)-3-methylphenyl)carbamateYield 81.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl chloroformate (0.416 g) in methylene chloride (1 ml) was added dropwise to a solution of 2-amino-6-methylbenzyl alcohol (0.549 g) and pyridine (0.364 g) in methylene chloride (10 ml) with ice cooling. After being stirred for 1 hour, the mixture was poured into 1N hydrochloric acid and extracted with methylene chloride. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The crystalline residue was washed with n-hexane and dried to give 2-methyl-6-methoxycarbonylaminobenzyl alcohol (0.64 g).

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. washThe crystalline residue was washed with n-hexane
  6. customdried

Sources & evidence

ORD record
ord-4fb57327d42946e894d21b1f71ca4162
Source dataset
uspto-grants-1990_04
Patent number
US04920129

Reaction notes

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